Topic 1:
Introduction to asymmetric synthesis; the fundamental concept of chirality and its importance in nature; how to assign the absolute configuration of a stereogenic centre (R)/(S). Types of chirality including axial chirality (allenes, atropisomeric biaryls, spiro compounds, alkylidene cycloalkanes) and planar chirality. Assignment of absolute configuration for planar and axial chirality.

Topic 2:
Introduction to selectivity in synthesis; the concept of topicity in selective synthesis (diastereotopic, enantiotopic), prochirality, Re and Si faces; the principle of asymmetric synthesis. Methods of asymmetric synthesis; classification as 1st (chiral pool), 2nd (chiral auxiliary), 3rd (chiral reagent) and 4th (asymmetric catalysis) generation methods; examples of 1st generation methods.

Topic 3:
Examples of 1st generation methods; cyclic cases (importance of conformation emphasised by conjugate addition reactions) and acyclic control (addition to C=C bearing an adjacent stereocentre); the importance of 1,3 allylic strain as a control element in epoxidation, hydroboration and enolate akylation reactions.

Topic 4:
Acyclic stereocontrol in the addition to C=O bearing an adjacent stereocentre); Cram’s rule (empirical) and Felkin Anh model (best); modifications of the Felkin-Anh rule (chelating groups, electronegative groups); substrate directed chemical reactions (epoxidation, cyclopropanation, aziridination) and 1,3 asymmetric induction in hydride reductions.

Topic 5:
2nd generation methods of asymmetric synthesis; the chiral auxiliary approach; what makes a good chiral auxiliary; examples (Schollkopf bis-lactim ethers); the importance of enolate geometry in asymmetric alkylations; stereoselective enolate formation (the Ireland deprotonation model); application to the alkylation of an oxazolidinone chiral auxiliary (Evans); the importance of chelation.

Topic 6:
Introduction to the aldol reaction; importance of enolate geometry in determining anti- or syn- relative configuration; the Zimmerman-Traxler model for aldol reactions; enolisation with boron enolates.

Topic 7:
The aldol reaction II; how can we control the enantioselectivity of the aldol reaction? A case study – using a chiral oxazolidinone; boron and titanium enolates; double diastereoselectivity in the aldol reaction