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COMPENDIUM OF CHIRAL AUXILIARY APPLICATIONS, THREE-VOLUME SET
Compendium of Chiral Auxiliary Applications, Three-Volume Set
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By
Greg Roos, Sultan Qaboos University, Sultanate of Oman

Description
The Compendium is a detailed compilation of chiral auxiliaries which are used in the field of organic chemistry to direct "asymmetric synthesis". A molecule is called chiral because it can have two "enantiomers" -- like left and right-handed molecules. An enantiomer is either of two molecules of the same chemical composition that are mirror images of each other but not identical. A "chiral auxiliary" is an aid / auxiliary used to specifically produce either the left or right enantiomer of the chosen molecule, as desired. In this comprehesive reference source, industrial chemists can make informed selections of an auxiliary for a specific application. It is fully cross-referenced to enable the comparative selection of auxiliaries. The work includes over 13,000 auxiliary reaction applications with complete reaction details of the synthetic routes, reagents, and primary literature references.

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

Contents
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-Buchi 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

Bibliographic details
Hardbound, 1423 pages, publication date: DEC-2001
ISBN-13: 978-0-12-595349-8
ISBN-10: 0-12-595349-6
Imprint: ACADEMIC PRESS

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