Aims

To familiarise students with the key strategies for the stereocontrolled synthesis of organic compounds; to provide practise in identifying and applying such strategies; to exemplify the principles in the context of the synthesis of organic targets

Outline Of Syllabus

Stereocontrol In Organic Synthesis

Introduction to synthetic strategy, selectivity and specificity
Regioselectivity
Stereoselectivity
The aldol reaction
Asymmetric synthesis. Use of the chiral pool
Seminar covering the material on Stereocontrol

Asymmetric Catalysis

Introduction to catalysis and asymmetric catalysis. Energy diagrams. Examples of commercial asymmetric catalytic procedures.
Chiral ligands. Ligand design & the use of C2 Ligand-symmetry.
Asymmetric catalysis of reduction reactions: Rh catalysed alkene hydrogenation. Ru catalysed ketone hydrogenation. Ketone reduction via Corey oxazaborolidines.
Asymmetric catalysis of oxidation reactions: Sharpless epoxidation; Jacobsen epoxidation. Sharpless bis-hydroxylation and aminohydroxylation.
Asymmetric catalysis of carbon-carbon bond forming reactions: Cycloaddition reactions. Addition of diethylzinc to aldehydes.
Organocatalysis. Enamine chemistry. Proline catalysed aldol reactions. Mannich reactions. Aldehyde amination and oxygenation. Michael additions.
Use of enzymes as catalysts. Whole cell and isolated enzymes. Need for cofactors. Oxidoreductases.
Asymmetric catalysis on compounds which already contain stereocentres. Kinetic resolution. Dynamic kinetic resolution. Desymmetrization of meso compounds. Double stereodifferentiation. Non-linear effects. Asymmetric autoinduction, asymmetric autocatalysis, asymmetric autoamplification.
Seminars covering questions on the material on Asymmetric Catalysis

Teaching Rationale And Relationship

The course involves the introduction of a set of principles which may be applied to the analysis and design of organic synthesis. These principles are addressed in the online lecture materials. These basic principles are consolidated in online material which exemplify these principles in the context of total synthesis of organic targets and serve to draw together the various strands of the course.

PiP delivery (3h per week) will be used to deliver the taught content and to provide feedback workshops discussing the answers to the provided online practise questions. Complete worked answers to these written problem-solving exercises are also published using a range of formats to support the learning. Short recordings of the key taught material are also provided online as an additional aid to revision.

Assessment Rationale And Relationship

The alternate written assessment will consist of problem-oriented questions, some of which focus on a particular principle or set of related principles and some which require broader analysis. This is deemed an appropriate method of ascertaining the principles introduced in the course and to the extent to which they can apply these to unfamiliar situations.

The formative assessment, problem-solving exercises, with their complete worked answers are published using a range of formats to support the learning.

Study Abroad students may request to take their exam before the semester 1 exam period, in which case the format of the paper may differ from that shown in the MOF. Study Abroad students should contact the school to discuss this.