Advanced Organic Synthesis
|Unit level:||Level 4|
|Teaching period(s):||Semester 1|
|Offered by||School of Chemistry|
|Available as a free choice unit?:||N
- 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
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
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.
- Written exam - 100%
- 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).
Students may work through the problem sheets supplied on Blackboard and submit answers to the lecturers for feedback.
- Assessment written exam - 2 hours
- Lectures - 24 hours
- Independent study hours - 74 hours