CHEM3205: Principles and Methods of Organic Synthesis

Course Organizer: Dr Tom Sheppard

Lecturers: Professor Jim Anderson, Dr Jon Wilden, Dr Tom Sheppard

Normal Prerequisite: CHEM2201

Units: 1/2 unit

Course Structure

  • Lectures: 26
  • Workshops: 6

Assessment

  • Exam: 80 % (2½ hours)
  • Coursework: 20%

Recommended Texts

As a main textbook, we recommend you use

  • “Organic Chemistry”; J Clayden, N Greeves, S Warren, OUP, 2012.

For more specialised information:

  • “Palladium Reagents and Catalysts” by J. Tsuji (Wiley)
  • “Molecular Orbitals and Organic Chemical Reactions” by Ian Fleming (Wiley)
  • “Pericyclic Reactions” by Ian Fleming (Oxford Chemistry Primer)
  • “Stereoelectronic Effects” by A. J. Kirby (Oxford Chemistry Primer)

Aims

The aim of this course is to give students an understanding of more advanced areas of organic synthesis. Key areas covered include: Palladium-catalysed reactions; Basic asymmetric synthesis; Pericyclic organic reactions; Stereoelectronic effects; and Stereocontrolled synthesis and manipulation of cyclic and polycyclic molecules.

Objectives

By the end of this course you should:

  • Understand how Palladium can be used to catalyse carbon-carbon and carbon-heteratom bond-formation.
  • Be familiar with the concept of asymmetric synthesis and the different strategies that can be used.
  • Know how to predict the outcome of simple diastereoselective and enantioselective reactions.
  • Understand what a pericyclic reaction is and how to explain the chemoselectivity, regioselectivity and stereoselectivity of simple pericyclic reactions.
  • Be able to explain why simple organic reactions are favourable/unfavourable due to stereoelectronic effects.
  • Know how to use stereoselective and regioselective reactions of decalins to synthesise a variety of products stereoselectively.
  • Know how selective reactions can be used to convert sugars into a variety of different molecules.

A. Catalytic Palladium Chemistry in Organic Synthesis (Prof. J. C. Anderson, 6 hours)

  • Introduction to transition metal chemistry in organic synthesis
  • Applications of Palladium-catalysed reactions in organic synthesis

Workshop 1

B. An Introduction to Asymmetric Synthesis (Dr. J. Wilden, 10 hours)

  • Introduction to asymmetric synthesis.
  • Geometrically controlled synthesis of alkenes.
  • Commonly used methods for asymmetric synthesis.

C. Frontier Orbitals in Organic Chemistry (Dr. J. Wilden)

  • Understanding orbital effects in organic reactions.
  • Hard and soft acids and bases.
  • Pericyclic reactions.

Workshop 2

D. Stereoelectronic Effects in Organic Synthesis (Dr T. D. Sheppard, 10 hours)

  • Stereoelectronic effects on structure and chemical reactivity.
  • Synthesis and reactions of saturated carbocyclic and heterocyclic ring systems.
  • Three-dimensional structures and their effect on reactivity – cis and trans decalins.
  • Selective chemical reactions of sugars – achieving regioselective reactions of poly-alcohols.

Workshop 3

There will also be some revision workshops towards the end of Term 2,