Undergraduate

modules

Modules

CHY8420 : Selectivity and Stereocontrol in Organic Synthesis

Semesters
Semester 1 Credit Value: 10
ECTS Credits: 5.0

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. Temperature dependence of asymmetric induction. Examples of commercial asymmetric catalytic procedures.
Chiral ligands. Ligand design. Ligand-symmetry. Energy diagrams for C1- and C2-symmetric processes.
Metals used in asymmetric catalysis. Role of the metal. What makes a good asymmetric catalyst?
Asymmetric catalysis of reduction reactions. Alkene hydrogenation. Ketone reduction.
Corey oxazaborolidines. Asymmetric catalysis of oxidation reactions. Sharpless epoxidation. Jacobsen epoxidation and related reactions.
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. Autocatalytic asymmetric induction. Absolute asymmetric synthesis.
Seminars covering questions on the material on Asymmetric Catalysis

Teaching Methods

Teaching Activities
Category Activity Number Length Student Hours Comment
Guided Independent StudyAssessment preparation and completion240:5020:00Revision for end of semester examination
Guided Independent StudyAssessment preparation and completion12:002:00End of semester examination
Scheduled Learning And Teaching ActivitiesLecture241:0024:00N/A
Guided Independent StudyIndependent study154:0054:00Background reading and practice past paper examination questions
Total100:00
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 20 lectures. These basic principles are consolidated in 4 seminars which exemplify these principles in the context of total synthesis of organic targets and serve to draw together the various strands of the course.

Assessment Methods

The format of resits will be determined by the Board of Examiners

Exams
Description Length Semester When Set Percentage Comment
Written Examination1201A100N/A
Assessment Rationale And Relationship

The written paper 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.

Reading Lists

Timetable