Postgraduate

Modules

Modules

CHY8834 : 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

Please note that module leaders are reviewing the module teaching and assessment methods for Semester 2 modules, in light of the Covid-19 restrictions. There may also be a few further changes to Semester 1 modules. Final information will be available by the end of August 2020 in for Semester 1 modules and the end of October 2020 for Semester 2 modules.

Teaching Activities
Category Activity Number Length Student Hours Comment
Guided Independent StudyAssessment preparation and completion201:0020:00Revision for end of module assessments
Guided Independent StudyAssessment preparation and completion11:001:00Completion of summative alternative assessment for first half of module content
Structured Guided LearningLecture materials11:001:00Online via Canvas - Module introduction, module structure, assessment, and reading lists
Structured Guided LearningLecture materials241:0024:00Online via Canvas - A combination of short recordings of lecture material and text published on VLE
Scheduled Learning And Teaching ActivitiesDrop-in/surgery11:001:00Week 15. (Thurs or Fri). Synchronous online support for assessment 2
Scheduled Learning And Teaching ActivitiesDrop-in/surgery11:001:00Week 11. Synchronous online support for assessment 1
Guided Independent StudyIndependent study151:0051:00Independent study
Guided Independent StudyIndependent study11:001:00Completion of summative alternative assessment for second half of module content
Total100:00
Jointly Taught With
Code Title
CHY8420Selectivity and Stereocontrol in Organic Synthesis
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 online 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

Please note that module leaders are reviewing the module teaching and assessment methods for Semester 2 modules, in light of the Covid-19 restrictions. There may also be a few further changes to Semester 1 modules. Final information will be available by the end of August 2020 in for Semester 1 modules and the end of October 2020 for Semester 2 modules.

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

Other Assessment
Description Semester When Set Percentage Comment
Computer assessment1M50alternate assessment - first half of module
Computer assessment1M50alternate assessment - second half of module
Assessment Rationale And Relationship

The alternate 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.

*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*

Reading Lists

Timetable