CHY8420 : Selectivity and Stereocontrol in Organic Synthesis
- Offered for Year: 2019/20
- Module Leader(s): Dr Julian Knight
- Lecturer: Dr Johan Eriksson
- Owning School: Natural and Environmental Sciences
- Teaching Location: Newcastle City Campus
|Semester 1 Credit Value:||10|
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
The aldol reaction
Asymmetric synthesis. Use of the chiral pool
Seminar covering the material on Stereocontrol
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.
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
|Guided Independent Study||Assessment preparation and completion||24||0:50||20:00||Revision for end of semester examination|
|Guided Independent Study||Assessment preparation and completion||1||2:00||2:00||End of semester examination|
|Scheduled Learning And Teaching Activities||Lecture||24||1:00||24:00||N/A|
|Guided Independent Study||Independent study||1||54:00||54:00||Background reading and practice past paper examination questions|
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.
The format of resits will be determined by the Board of Examiners
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.