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The University of Southampton

CHEM6161 Stereoselective Reactions

Module Overview

Aims and Objectives

Learning Outcomes

Learning Outcomes

Having successfully completed this module you will be able to:

  • Be able to explain the concept of retrons, and advanced retrosynthesis principles including stereochemical aspects
  • Be able to explain key principles behind enantio- and diastereoselectivity, and develop skills to establish how the stereochemical outcome of reactions can be predicted
  • Demonstrate your understanding of the principles behind enantioselective synthesis
  • Be able to explain a range of approaches to synthesis that exploit the properties of other elements (particularly phosphorous, sulphur, silicon,
  • Predict reaction pathways and outcomes on the basis of mechanistic understanding.


The syllabus, which is outlined below, is aligned with the following QAA benchmark statements for chemistry at FHEQ Level 7 (Masters). • To extend students' comprehension of key chemical concepts and so provide them with an in-depth understanding of specialised areas of chemistry; • To develop in students, the ability to adapt and apply methodology to the solution of unfamiliar types of problems; • To instill a critical awareness of advances at the forefront of the chemical science discipline; • To prepare students effectively for professional employment or doctoral studies in the chemical sciences; • To extend their knowledge base to provide a systematic understanding and critical awareness of topics which are informed by the forefront of the discipline; • Problems of an unfamiliar nature are tackled with appropriate methodology and taking into account the possible absence of complete data. This is a research-led module and the lectures cover stereoselective methodologies. Each Methodology is explained in detail and illustrated through synthetic examples. In addition, some concepts seen in earlier modules, such as retrosynthetic analysis, will be expanded to include stereochemical aspects and strategic disconnections such as the use of molecules and reagents containing Sulphur, Selenium, Silicon, and Phosphorous in organic synthesis with an emphasis on stereoselective alkene synthesis (Peterson reaction, sylil ketene acetals, Arbuzov reaction, Horner–Wadsworth–Emmons reaction, Still-Gennari reaction, Alkene synthesis via Julia coupling and Ramberg–Bäcklund reaction. Pummerer rearrangement for example) This is a course for students who are interested to pursue a career in synthetic organic chemistry (including all areas involving molecular synthesis. Some examples are: process development chemistry, medicinal chemistry, agrochemistry, fine chemicals and so on). Emphasis will be placed on developing the skills to identify and apply diastereoselective and enantioselective reactions to build chiral target molecules. A focus is on investigating transition states to explain transfer of chirality, in a synthetic setting. It includes chiral auxiliaries, chiral catalysts (transition metal catalysts and organocatalysts), as well as simply starting from the chiral pool. Examples covered include: Diels-Alder reaction, aldol reactions controlled by Evans auxiliaries, enamine and imine organocatalysis, Sharpless asymmetric epoxidation and dihydroxylation, allylic strain, and Carbene catalysis.

Learning and Teaching

Teaching and learning methods

Teaching methods: Lectures, directed reading, Blackboard online support. Learning methods: Independent study, student motivated peer group study

Preparation for scheduled sessions60
Follow-up work40
Total study time150



MethodPercentage contribution
Final Assessment  100%


MethodPercentage contribution
Final Assessment  100%

Repeat Information

Repeat type: Internal & External

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