COMPENDIUM OF CHIRAL AUXILIARY APPLICATIONS – 3 VOLS

Partial TOC –
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

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

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

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

REACTION OF PHOSPHORIC ACID DERIVATIVES WITH ALKYL AND OTHER ELECTROPHILES
a-Alkylation
Alkyl and aralkyl derivatives
a-Chloro derivatives
a-Amino derivatives

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

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

ENE REACTIONS
ADDITION OF HALO-CONTAINING ADDENDS
Halogenation
Halohydrin formation
Halolactonization

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

CYCLOPROPENATION
RADICAL ADDITION
Auxiliary on acceptor alkene
Intermolecular
Intramolecular

CONJUGATE AND RELATED ADDITION TO ELECTROPHILIC C=C BONDS
Auxiliary on the donor nucleophile – simple addition
Acyl anion equivalents
Formyl derivatives