This module consists of a range of examples exposing the students to sophisticated methods in stereoselective synthesis. Building on previous knowledge, advanced methods for stereocontrol in total synthesis, preparation of enantiomerically pure drug molecules, development of stereoselective rearrangement processes as well as the introduction of various enabling technologies will be the main focus of this module. Throughout, the ability to extract stereochemically relevant information from complex syntheses will be a major focus.

Knowledge

• Appreciate the range of synthetic methods available to prepare enantiomerically pure molecules.
• Know the strategies and reagents required to generate and implement new stereochemical elements within target-oriented syntheses.
• Identify key problems in both small-scale academic synthesis and large scale industrial synthesis of stereochemically pure compounds.
• Identify different reaction technology equipment and summarise the key criteria to consider before using it.

Understanding

• Understand the principles and strategies of stereoselective alkene functionalization.
• Understand main principles in the use of enabling technologies and related industrial issues together with application to target molecules.
• Recognize where organocatalysis can be applied in synthesis and which strategies in this area are available.
• Explain when alternative tools and techniques may offer significant benefit to a desired reaction outcome.

This module will be delivered in 10 two-hour lectures, supplemented by 4 1-hour class tutorials, and consists of three blocks, each covering a different aspect of asymmetric synthesis. An initial set of lectures will be used to revise already known principles and reactions and introduce novel methods that can be used to tackle certain problems in asymmetric synthesis together with their theoretical background and any strengths or weaknesses associated with them. These will be followed by three units in which such methods are applied to chemical problems.

Ability to analyse stereochemical problems and provide synthetic solutions.

The module is summatively assessed via in course assessments.

There is no examination for this module.

Alkene Functionalisations

Introduction to advanced asymmetric synthesis. Stereoselective functionalisations of double bonds: Briefly revising Sharpless AE and ADH, Jacobsen (year 3), then introduction of other electrophilic reagents including selenium- and iodine-based compounds.  Applications in total synthesis and the synthesis of bioactive compounds will be discussed.

Enabling Tools for Organic Synthesis

As synthesis moves in to the modern era so too does the way in which chemists can conduct chemistry. This part of the course introduces the technical considerations needed for using existing and futuristic synthesis tools such as microwave reactors, photochemical reactors, electrochemistry and continuous flow chemistry. Important factors are being considered when conducting reactions using these methods, there will also be a strong focus on the types of synthetic chemistry suited to these modes.

Organocatalysis

Organocatalysis is defined as the use of a sub-stoichiometric amount of an organic molecule to accelerate the rate of a chemical reaction. This part will serve as an introduction to the diverse and exciting field of organocatalysis and will specifically cover: a historical perspective; benefits and limitations; catalyst synthesis; covalent and non-covalent organocatalytic activation modes; selectivity (regio-, diastereo- and enantiocontrol); applications within industry; applications towards the synthesis of biologically active compounds.