»
Key Chiral Auxiliary Applications
 
 

Key Chiral Auxiliary Applications, 2nd Edition

 
Key Chiral Auxiliary Applications, 2nd Edition,Gregory Roos,ISBN9780124170346
 
 
 

  

Academic Press

9780124170346

9780124171152

1270

276 X 216

This compilation allows the reader to make carefully informed selections of an auxiliary for a specific asymmetric synthetic transformation without spending hours searching many resources.

Print Book + eBook

USD 330.00
USD 550.00

Buy both together and save 40%

Print Book

Hardcover

In Stock

Estimated Delivery Time
USD 275.00

eBook
eBook Overview

DRM Free included formats: EPub, Mobi, PDF

VST format:

USD 275.00
Add to Cart
 
 

Key Features

  • Provides a comprehensive compilation based on nearly 40,000 diverse applications of chiral auxiliaries for selecting the best synthetic route to optically pure compounds
  • Contains over 60% new material with 13,000+ auxiliary applications categorized by reaction type, with reaction details and chemical and optical yields in one unique resource

Description

Key Chiral Auxiliary Applications, Second Edition is a detailed compilation of chiral auxiliary applications organized by type of transformation. Continuing from the most important and relevant auxiliaries described in its predecessor, the three-volume set Compendium of Chiral Auxiliary Applications (2001), as well as advances in the field, the book provides a vital and timely resource for chemists in the field. Each reaction class includes a series of tables and graphical abstracts of real reactions from the literature and patents to enable easy review and comparison of results. This anticipated edition is based on a screening of nearly 40,000 auxiliary reaction applications, with details supplied for the more than 13,000 selected representative entries: synthetic route, reagents, yields, diastereomeric/enantiomeric excesses, and characterization data.  Updated and streamlined with more than 60% new material, Key Chiral Auxiliary Applications provides valuable guidance and reliable content for selecting the best auxiliary for a specific asymmetric synthetic transformation.

Readership

Industrial, organic, and pharmaceutical chemists in industry and academia.

Gregory Roos

Greg Roos’ formal education comprised of a BSc (1971), BSc Honours (1972), and PhD in Organic Synthesis (1976) from the University of Cape Town. A postdoctoral fellowship with Richard Cookson at the University of Southampton was followed by a few years of pharmaceutical industrial experience. His fulltime academic career involved the University of Natal, South Africa (1981-1994), Murdoch University, Australia (1994-1997), and an extended period in the Middle East, including Sultan Qaboos University, Oman (1998-2004) and The Petroleum Institute, Abu Dhabi (2004-2008). He has successfully taught across various cultures and has received awards for his teaching contributions and innovations. Since 2009, as an adjunct Professor at Murdoch University, he shares his time between Australia and Dubai. His research interests have focused on the development of synthetic methodology, with particular interest in asymmetric processes. This provided numerous publications in the areas of the Baylis-Hillman reaction, imidazolidinone chiral auxiliaries, and dirhodium catalyst development and applications. This period also included a number of productive collaborative visits with Tony McKervey (University College Cork & Queen’s University, Belfast), C. K. Sha (Shin Hua University, Taiwan), Mike Doyle (Trinity University, San Antonio), and Ron Warrener (CQU Rockhampton, Queensland). In 2001 he received the Merck Gold Medal for research from the South African Chemical Institute.

Affiliations and Expertise

Murdoch University, Perth, Western Australia

Key Chiral Auxiliary Applications, 2nd Edition

ALKYLATION AND RELATED REACTIONS
REACTIONS OF ALLYL AND BENZYL RELATED CARBANIONS WITH ALKYL AND ACYL ELECTROPHILES
Alkylation of allyl and benzyl derivatives
Alkylation of allyl, benzyl and related amines
Via aminooxazolines
Via formamidines
Other derivatives
Allyl related systems
Benzyl related systems
Reaction of allyl ether equivalents
a-Alkylation
a-Acylation
Other electrophiles
Alkylation of vinyl ethers
a-Alkylation of allyl and benzyl related silanes
Allenic ether tandem acylation-cyclization
REACTIONS OF ALDEHYDE DERIVATIVES WITH ALKYL AND OTHER ELECTROPHILES
Simple aldehydes
a-Alkylation
Via hydrazone derivatives
Via imine and enamine derivatives
a-Hydroxylation
a-Silylation
Sequential silylation + alkylation
a-Phosphinylation
a-Thiolation
a-Heterosubstituted aldehydes
a-Alkylation
a-Amino derivatives
a-Oxy derivatives
Sequential alkylation + nucleophilic addition
a-Silyl derivatives - sequential reactions
Alkylation + alkylation
Alkylation + acylation
a-Phosphino derivatives
a-Thio derivatives
Sequential alkylation + acylation
REACTION OF KETONE DERIVATIVES WITH ALKYL AND OTHER ELECTROPHILES
a-Alkylation
Acyclic systems with auxiliary on the ketone
Simple ketone derivatives
b-Dicarbonyl derivatives
b-Keto ester derivatives
Cyclic systems with auxiliary on the ketone
Simple ketone derivatives
Cyclopentanone derivatives
Cyclohexanone derivatives
Higher order cyclic ketones
b-Dicarbonyl derivatives
b-Keto ester and equivalent derivatives
a-Heteroatom substituted ketone derivatives
a-Dicarbonyl and related derivatives
a-Nitronate substituted derivatives
a-Thio substituted derivatives
a,a¢-Diamino substituted derivatives
a,a¢-Dioxy substituted derivatives
Reaction with other electrophiles
a-Acylation
a-Amination
a-Hydroxylation
a-Silylation
Sequential silylation + alkylation
a-Phosphinylation
a-Halogenation
REACTION OF CARBOXYLIC ACID DERIVATIVES WITH ALKYL AND OTHER ELECTROPHILES
a-Alkylation
C2-Acid derivatives (acetate equivalents)
Creation of an a-stereocentre (sequential bisalkylation)
Creation of a b-stereocentre (kinetic resolution and related)
Phenylacetic acid derivatives
Unsubstituted phenyl ring derivatives
Aromatic ring-modified derivatives
Other related derivatives
C3-Acid derivatives (propionate equivalents)
Reaction with C1-electrophiles
Methyl derivatives
Benzyl derivatives
Reaction with C2-electrophiles
Ethyl derivatives
Substituted ethyl derivatives
Reaction with C3-electrophiles
Propyl and substituted propyl derivatives
Allyl and related derivatives
Reaction with C4-electrophiles
Butyl derivatives
Substituted butyl derivatives
Reaction with C5-electrophiles
Reaction with higher order electrophiles
Reaction with sundry heterocyclic electrophiles
Phenylpropionic acid derivatives
Unsubstituted phenyl ring derivatives
Aromatic ring-modified derivatives
Malonic acid and related derivatives
Bisalkylation of unsubstituted derivatives
Reaction of monosubstituted derivatives
Reaction of miscellaneous substituted C3-acid derivatives
b-Oxo acid derivatives
Acyclic systems
Cyclic systems
C4-Acid derivatives
Unsubstituted butanoic acid derivatives
Unsaturated and carbon substituted derivatives
Succinic acid and related derivatives
Other heteroatom substituted derivatives
C5-Acid derivatives
Unsubstituted pentanoic acid derivatives
Unsaturated and carbon substituted derivatives
Heteroatom substituted derivatives
C6-Acid derivatives
Unsubstituted hexanoic acid derivatives
Unsaturated and carbon substituted derivatives
Heteroatom substituted derivatives
Higher order acid derivatives
a-Amino acid derivatives
Auxiliary on the acid
Glycinate equivalents
Alanate equivalents
Higher order amino acid equivalents
Auxiliary on the nitrogen
Glycinate equivalents
Alanate equivalents
Higher order amino acid equivalents
Auxiliary on both acid and nitrogen
Individual auxiliaries
Single auxiliary (bislactim ethers / cyclic Schiff bases / oxazinones)
Glycinate equivalents
Alanate equivalents
Higher order amino acid equivalents
Other a-heteroatom substituted acid derivatives
a-Oxy derivatives
Glycolic acid derivatives
Higher order derivatives
a-Thio derivatives
a-Halogeno derivatives
a-Silyl derivatives
Lactones
Lactams
Monofunctional systems
Bicyclic lactams (g- and d-oxo acid derivatives)
a-Acylation of acid derivatives
a-Amination of acid derivatives
Electrophilic amino equivalents with the auxiliary on the nucleophile
Electrophilic amino equivalents with the auxiliary on the electrophile
Nucleophilic amino equivalents (halogenation + substitution)
a-Amination of phosphonic acid derivatives
a-Hydroxylation of acid derivatives
a-Silylation of acid derivatives
a-Thiolation of acid derivatives
a-Selenation of acid derivatives
a-Halogenation of acid derivatives
REACTION OF PHOSPHORIC ACID DERIVATIVES WITH ALKYL AND OTHER ELECTROPHILES
a-Alkylation
Alkyl and aralkyl derivatives
a-Chloro derivatives
a-Amino derivatives
Auxiliary on nitrogen
Auxiliary on phosphorus
a-Amination
a-Halogenation
ALKYLATION OF SULFONAMIDES WITH THE AUXILIARY ON NITROGEN
MISCELLANEOUS RELATED REACTIONS
Protonation of auxiliary-bearing substrates
Dynamic kinetic resolution with auxiliary-bearing electrophiles
Carbon nucleophiles
Nitrogen nucleophiles
Oxy-nucleophiles
Thio-nucleophiles
Halo-nucleophiles
Wittig-type reactions
Deracemization via acylation
Sundry reactions of acid derivatives with auxiliary-bearing electrophiles
Friedel-Crafts type reactions
Reaction of arenechromium tricarbonyl carbanions with alkyl and hetero electrophiles
Aromatic substitution
Nucleophilic
Radical
REFERENCES

ADDITION TO C=C BONDS
REDUCTION AND RELATED REACTIONS
Catalytic hydrogenation
Carbon substituted a,b-unsaturated acyl derivatives
Heteroatom substituted a,b-unsaturated acyl derivatives
a-Nitrogen substituted
b-Nitrogen substituted
b-Oxygen substituted
Aromatic systems
Dissolving metal reduction of aromatic systems
Tandem reductive alkylation of acyl substituted aromatic systems
ENE REACTIONS
ADDITION OF HALO-CONTAINING ADDENDS
Halogenation
Halohydrin formation
Halolactonization
Other
DIHYDROXYLATION
Mono- and disubstituted C=C
Trisubstituted C=C
EPOXIDATION
Monosubstituted C=C
Disubstituted C=C
Trisubstituted C=C
CYCLOPROPANATION
Auxiliary on acceptor
Mono- and disubstituted acyclic alkenes
Trisubstituted acyclic alkenes
Cycloalkenes with unsubstituted C=C
Cycloalkenes with substituted C=C
Auxiliary on donor
Intramolecular
Tandem cyclopropanation + rearrangement
CYCLOPROPENATION
RADICAL ADDITION
Auxiliary on acceptor alkene
Intermolecular
Intramolecular
Auxiliary on donor radical
Intermolecular
Intramolecular
CONJUGATE AND RELATED ADDITION TO ELECTROPHILIC C=C BONDS
Auxiliary on the donor nucleophile - simple addition
Acyl anion equivalents
Formyl derivatives
Higher order derivatives
Aldehyde-derived enolate equivalents
Ketone-derived enolate equivalents
Alkyl ketone derivatives
Aralkyl ketone derivatives
Cyclic ketone derivatives
1,3-Dicarbonyl derivatives (b-keto esters and b-diketones)
Intramolecular reactions
Acyl enolate equivalents
Simple acyl derivatives
Lactam and lactone derivatives
Intramolecular reactions
a-Amino acid derivatives - auxiliary on nitrogen (glycinate and alaninates)
a-Amino acid derivatives - auxiliary bonded to both acyl and nitrogen (bislactims and Ni complexes)
a-Alkoxy acyl derivatives (glycolates)
Conjugated phosphonamide anions (allyl/crotyl)
Transition metal complexed aryl nucleophiles
Nitrogen heteronucleophiles
Auxiliary on the donor nucleophile - tandem addition
Acyl-anion equivalents - conjugate addition + alkylation
Carbonyl-based donor nucleophiles
Conjugate addition + alkylation
Conjugate addition + acylation
Conjugate addition + aldol reaction
Others
Acyl enolate equivalents
Nitrogen heteronucleophiles - conjugate addition + alkylation
Auxiliary on donor - radical addition
Auxiliary on acceptor a,b-unsaturated system - simple addition
a,b-Unsaturated aldehyde-based derivatives
Addition of carbon nucleophiles
Addition of heteronucleophiles
a,b-Unsaturated ketone-based derivatives
a,b-Unsaturated acyl derivatives - addition of carbon nucleophiles
Acrylic / methacrylic and related derivatives
Crotonic and tiglic acid derivatives
Addition of aliphatic nucleophiles
Addition of aromatic nucleophiles
Phenyl organometallic reagents
Substituted phenyl organometallic reagents
Malonic and b-keto ester derivatives
Higher order aliphatic acyl derivatives
Unfunctionalized acyl derivatives
Functionalized derivatives
a,b-Unsaturated aromatic acyl derivatives
Cinnamic acid and related derivatives
Reaction of organometallic reagents
Reaction of enolate derivatives
Substituted aromatic and heteroaromatic derivatives
b-Heteroatom substituted derivatives
a,b-Unsaturated acyl derivatives - addition of heteronucleophiles
Hydride (conjugate reduction)
Nitrogen derivatives
Alkoxides
Thiolates
Silyl anions
Halides
Other activated systems
a,b-Unsaturated sulfoximine and sulfonic acid derivatives
a,b-Unsaturated nitro derivatives (addition/elimination)
Activated aromatic acid derivatives
1,4-Addition to pyridinium systems
N-alkyl derivatives
N-acyl derivatives
Intramolecular reactions
Auxiliary on acceptor a,b-unsaturated system - tandem addition of carbon nucleophiles
Carbonyl-based derivatives - conjugate addition + alkylation
Acyl-based derivatives
Conjugate addition + alkylation
Conjugate addition + acylation/amination/hydroxylation/thiolation/ halogenation
Conjugate addition + conjugate addition
Conjugate addition + C=N addition
Conjugate addition + aldol reaction
Conjugate addition + miscellaneous
Auxiliary on acceptor a,b-unsaturated system - tandem addition of heteronucleophiles
Conjugate addition + alkylation
Hydride (reductive alkylation)
Nitrogen derivatives
Tin derivatives
Conjugate addition + others (conjugate addition / acylation / aldol / halogenation)
Auxiliary on acceptor a,b-unsaturated system - radical addition
Nucleophilic addition to transition-metal alkene/arene complexes
Auxiliary on the donor nucleophile
Auxiliary on the acceptor transition-metal complex
REFERENCES

ADDITION REACTIONS TO C=N BONDS
REDUCTION OF IMINES, IMINIUM IONS, HYDRAZONES AND OXIMES
ENE REACTIONS
NUCLEOPHILIC ADDITION
Imines and oximes - auxiliary on nitrogen
Carbon-based nucleophiles
Phosphite nucleophiles
Imines and oximes - auxiliary on carbon
Glyoxal and glycolate derivatives
Pyruvaldehyde derivatives
Others
Imines - auxiliary on nucleophile
Addition of simple enolate equivalents
Acetate and related derivatives
Propionate and related derivatives
Higher order derivatives
Addition of a-heteroatom substituted enolates
a-Amino derivatives
a-Alkoxy derivatives
a-Thio derivatives
Addition of aryl organometallics
Iminium derivatives
Intermolecular 1,2-addition
N-Acyl anilinium derivatives
N-Acyl piperidinium derivatives
N-Acyl pyridinium derivatives
N-Acyl isoquinolinium derivatives
Auxiliary on nucleophiles
Intramolecular 1,2-addition
Hydrazones
Simple alkyl/aryl aldehyde derivatives
a-Amino and a-alkoxy substituted aldehyde derivatives
a,a-Heteroatom substituted hydrazones (glyoxal and pyruvaldehyde derivatives)
Auxiliary on nitrogen
Auxiliary on carbon
Hydrazonium derivatives
Nitrone derivatives
RADICAL ADDITION
Hydrazones
Oximes
REFERENCES

ADDITION REACTIONS TO C=O BONDS
REDUCTION
a-Alkoxy ketones
a-Keto aldehydes
1,2-Diketones
a-Keto acid derivatives
b-Aminoketones
b-Keto aldehydes
b-Keto acid derivatives
w-Keto acid derivatives
ENE REACTIONS
WITTIG AND RELATED OLEFINATION
ADDITION OF ORGANOMETALLIC AND RELATED REAGENTS
Auxiliary-bearing acceptor carbonyl derivatives
1,2-Dicarbonyl derivatives
a-Oxo acid derivatives
Related aminals and acetals
1,n-Hydroxycarbonyl derivatives
1,n-Dicarbonyl derivatives
w-Acyl carbonyl derivatives
Auxiliary-bearing organometallic donor reagents
Acyl anion equivalents (formyl, acetyl, acryloyl, benzoyl)
Allylic and benzylic related derivatives
Formamidines
Aromatic derivatives
ADDITION OF ENOLATES (ALDOL AND RELATED REACTIONS)
Auxiliary-bearing acceptor carbonyl derivatives
Auxiliary-bearing enolate equivalents from carbonyl precursors
Creation of a single stereocentre
Creation of two stereocentres
Auxiliary-bearing enolate equivalents from carboxylic acid precursors
Acetate equivalents - creation of a single stereocentre
Reaction with alkyl aldehydes
Reaction with a,b-unsaturated aldehydes
Reaction with aromatic aldehydes
Reaction with a- or b-heteroatom functionalized aldehydes
Reaction with ketones
Priopionate equivalents - creation of two stereocentres
Reaction with alkyl aldehydes
Reaction with a,b-unsaturated aldehydes
Reaction with aromatic aldehydes
Reaction with a- or b-heteroatom functionalized aldehydes
Reaction with ketones
Higher order equivalents
Creation of a single stereocentre
Creation of two stereocentres
Phenacyl and phenethyl derivatives
Others
a,b- and b,g-Unsaturated acyl enolate equivalents
Acryloyl derivatives (Baylis-Hillman and related reactions)
Crotonyl and related derivatives
Auxiliary-bearing a-heteroacyl derivatives
a-Amino acid derivatives - auxiliary bound to acyl
a-Amino acid derivatives - auxiliary bound to nitrogen
a-Amino acid derivatives - auxiliary on both acid and nitrogen (bislactim ethers / cyclic Schiff bases)
a-Alkoxy derivatives
a-Thio derivatives
a-Halo derivatives
Homoenolate equivalents
TANDEM REACTIONS
RADICAL REACTIONS
Addition to auxiliary-bearing acceptor carbonyl derivatives
Addition by auxiliary-bearing donor radical derivatives
Intramolecular addition
Coupling reactions
REFERENCES

CYCLOADDITIONS
[2+2]-CYCLOADDITIONS
Photochemical reactions
Intermolecular cyclobutane formation
Intramolecular cyclobutane formation
Oxetane formation (Paterno-Büchi reaction)
Reactions of ketene-based derivatives
Reaction of ketenes with auxiliary-bearing alkenes
Reaction of ketene acetals/thioacetals with auxiliary-bearing alkenes
Reaction of auxiliary-bearing ketenes with imines (Staudinger reaction)
Reaction of keteniminium derivatives with alkenes
Intermolecular cyclobutanone formation
Intramolecular cyclobutanone formation

[3+2]-CYCLOADDITIONS
Photochemical reactions
Alkyl diazo dipoles - reaction with auxiliary-bearing C=C dipolarophiles
Nitrile oxide dipoles
Alkyl nitrile oxide dipoles with C=C dipolarophiles
Acrylic acid-derived dipolarophiles
Higher order enoyl dipolarophiles
Vinyl ether dipolarophiles
Aryl nitrile oxide dipoles with C=C dipolarophiles
Acrylic acid-derived dipolarophiles
Higher order enoyl dipolarophiles
Vinyl ether dipolarophiles
Aryl nitrile oxide dipoles with C=N dipolarophiles
Acyl and halo nitrile oxide dipoles
Nitrilimine dipoles - reaction with auxiliary-bearing C=C dipolarophiles
Nitrone dipoles
Auxiliary on C=C dipolarophile
Auxiliary on the nitrone dipole
Silyl nitronate dipoles - reaction with auxiliary-bearing C=C dipolarophiles
Azomethine and related ylide dipoles
Auxiliary on the C=C dipolarophile
Acrylic acid derivatives
Higher order enoyl derivatives
Auxiliary on the ylide dipole
Thiocarbonyl ylides
Sundry transition metal-mediated equivalents
[4+2]-INTERMOLECULAR HOMO-CYCLOADDITIONS (DIELS-ALDER REACTIONS) - AUXILIARY ON THE DIENOPHILE
Acrylic acid derived dienophiles with acyclic dienes
Butadiene
Monosubstituted butadienes
Disubstituted butadienes
Acrylic acid derived dienophiles with cyclic dienes
Cyclopentadienes
Cyclohexadienes
Heterocyclic dienes
Miscellaneous dienes
Methacrylic acid derived dienophiles
Other a- or b-substituted acrylic derived dienophiles
Allene derived dienophiles
Crotonic acid derived dienophiles
Acyclic dienes
Cyclic dienes
Cinnamic and related aromatic acid derived dienophiles
Fumaric and maleic acid derived dienophiles
Acyclic dienes
Cyclic dienes
Miscellaneous acyl-derived dienophiles
Heteroatom substituted non-acyl dienophiles (allyl amines/ethers)
Cyclic dienophiles
Tandem processes
[4+2]-INTERMOLECULAR HOMO-CYCLOADDITIONS (DIELS-ALDER REACTIONS) - AUXILIARY ON THE DIENE
Acyclic dienes
2,4-Pentdienoic acid derivatives
N-functionalized dienes (enamine)
N,O- functionalized dienes (enamine/enol ether)
O- functionalized dienes (enol ether)
O,O- functionalized dienes (ketene acetal/enol ether)
S- functionalized dienes (sulfixyl)
S,O- functionalized dienes (sulfinyl/enol ether)
Cyclic dienes
[4+2]-INTRAMOLECULAR HOMO-CYCLOADDITIONS (DIELS-ALDER REACTIONS)
[4+2]-HETERO-CYCLOADDITIONS (HETERO-DIELS-ALDER REACTIONS)
Auxiliary on dienophile
N in heterodiene
O in heterodiene
S in heterodiene
N/O in heterodiene
N/S in heterodiene
N/N/O in heterodiene
Auxiliary on heterodienophile
N in heterodienophile
O in heterodienophile
S in heterodienophile
N/O in heterodienophile
N/S in heterodienophile
Auxiliary on diene
N in heterodienophile
O in heterodienophile
S in heterodienophile
N/N in heterodienophile
N/O in heterodienophile
O/O in heterodienophile
Auxiliary on heterodiene
N in heterodiene
O in heterodiene
S in heterodiene
N/O in heterodiene
[4+3] CYCLOADDITIONS
[6+2]- AND [6+4]-CYCLOADDITIONS
REFERENCES

REARRANGEMENTS
[2,3]-SIGMATROPIC VARIANTS
Wittig rearrangement
Meisenheimer rearrangement
Other rearrangements
[3,3]-SIGMATROPIC VARIANTS
Carroll rearrangement
Claisen rearrangement
Aza-Claisen rearrangement
Thia-Claisen rearrangement
Cope / oxy-Cope / siloxy-Cope rearrangement
Other rearrangements
REFERENCES

MISCELLANEOUS REACTIONS
SUNDRY ENE REACTIONS
TRANSITION-METAL CONTROLLED REACTIONS
Carbene insertion reactions
C-H Insertions
N-H Insertion
O-H Insertion
Si-H Insertion
Coupling reactions
Coupling of allyl derivatives
Coupling of aryl derivatives
Cyclization reactions
Heck reactions
Pauson-Khand reactions
Miscellaneous cyclizations
Sulfoxide preparation from sulfides
Elimination reactions
REFERENCES
 
 
Cyber Monday SALE Upto 50 Percent OFF | Use Code CYBER14
Shop with Confidence

Free Shipping around the world
▪ Broad range of products
▪ 30 days return policy
FAQ

Contact Us