Advanced Organic Synthesis


Unit code: CHEM40411
Credit Rating: 10
Unit level: Level 4
Teaching period(s): Semester 1
Offered by School of Chemistry
Available as a free choice unit?: N

Requisites

None

Aims

  • To provide an up-to-date account of modern methods synthetic organic chemistry
  • To cover key transformations in depth and to put them in context in synthesis
  • To cover the strategies employed in the total synthesis of complex natural products

Overview

Heteroelement Chemistry in Synthesis (Dr A C Regan, 8 lectures)

  • Organosulfur chemistry in synthesis: reactions and methods using sulfoxides and sulfur ylides
  • Organosilicon methods: allyl silanes and vinyl silanes. Silicon as a “superproton”
  • Organoboron methods: hydroboration reactions; boranes and allylborane reagents
  • Case studies and applications in synthesis

Asymmetric Synthesis (Dr D Leonori, 8 lectures)

  • the Chiral Pool: exploiting the molecules of nature sugars & amino acids as starting materials
  • asymmetric functionalisation of prochiral units, asymmetric C-C bond formation
  • Chiral Auxiliaries: recyclable chirality, asymmetric alkylation of enolates, asymmetric aldol reactions
  • chiral reagents and chiral catalysts: asymmetric hydroboration, asymmetric oxidations (epoxidation, dihydroxylation) and reductions (the CBS catalyst, Ru-catalysed reduction, asymmetric hydrogenation)
  • ligand-accelerated catalysis and organocatalysis
  • examples of biologically and commercially important syntheses of drugs and of natural products based on asymmetric methods

Total Synthesis (Dr A Pulis, 8 lectures)

  • The importance and value of total synthesis
  • Planning synthesis by recognising key disconnections based on the functional groups present
  • Strategic application of named and common organic reactions in complex settings
  • Rationalising substrate controlled stereoselectivity
  • Reagents used to interconvert common functional groups
  • The power of ring forming reactions
  • Multicomponent and cascade reactions

Learning outcomes

 Students should be able to:

  • Appreciate how modern synthetic organic chemistry is conducted
  • Propose plausible synthetic strategies or routes to complex organic structures
  • Propose suitable reagents for given transformations
  • Be able to suggest mechanistic or strategic rationales for given synthetic routes
  • Understand the stereochemical principles on which asymmetric synthesis is based
  • Have an appreciation of the importance and value of total synthesis
  • Understand the use of selected heteroelements, both metals and non metals, to facilitate synthetic transformations.

Transferable skills and personal qualities

Problem solving skills will be developed throughout the course unit, using the problem sheets provided by the lecturers, and will involve applying the information learned to unseen organic transformations and syntheses.

Assessment methods

  • Written exam - 100%

Recommended reading

  • Clayden, Greeves, Warren and Wothers, Organic Chemistry, 2nd edition, Oxford University Press, 2012.
  • S E Thomas, Organic Synthesis. The Roles of Boron and Silicon, Oxford University Press, 1991.
  • March's Advanced Organic Chemistry, Michael B. Smith and Jerry March, Wiley, (5th and 6th editions: several copies available in University Library; 6th edition also available for reading online via Library website).

Feedback methods

Students may work through the problem sheets supplied on Blackboard and submit answers to the lecturers for feedback.

Study hours

  • Assessment written exam - 2 hours
  • Lectures - 24 hours
  • Independent study hours - 74 hours

Teaching staff

Daniele Leonori - Unit coordinator

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