Module Details
The information contained in this module specification was correct at the time of publication but may be subject to change, either during the session because of unforeseen circumstances, or following review of the module at the end of the session. Queries about the module should be directed to the member of staff with responsibility for the module.
Title ASYMMETRIC SYNTHESIS AND MAIN GROUP ORGANIC CHEMISTRY (P, S, SE); C OPTION
Code CHEM433
Coordinator Dr C Aissa
Chemistry
Christophe.Aissa@liverpool.ac.uk
Year CATS Level Semester CATS Value
Session 2014-15 M Level First Semester 7.5

Aims

The aim of this module is to further broaden and extend the knowledge of modern Organic Chemistry so that students will be able to enter directly into a PhD or embark on a career as a specialist chemist.


Learning Outcomes

By the end of the module students will have achieved a solid foundation in Organic Chemistry. In particular they will have a clear understanding of

(a) Asymmetric Synthesis

(b) Main Group Organic Chemistry (P, S, Se)

and be able to give examples of their use in modern synthetic methodology.


Syllabus
1  Asymmetric Synthesis
  • Introduction to strategies: Resolution, Analysis, Chiral pool.
  • Chiral auxiliaries Evans oxazolidinones- Diels-Alder, enolates, aldol
  • Chiral reagents Reduction (BINAL), Hydroboration (Brown) Allylation and Crotylation (Brown, Roush, Corey)
  • Chiral catalysts Reduction (CBS), Hydrogenation (BINAP), Isomerisation (menthol production), Organozinc additions to aldehydes (Noyori), Epoxidation (Sharpless, Katsuki-Jacobsen) , Dihydroxylation (Sharpless), Palladium catalysed processes (Heck, allylation, etc.), Lewis acid catalysts (Diels-Alder, etc.)
  • Applications to total synthesis Topical examples to exemplify the power of the methodology.

Main Group Organic Chemistry

  • Che mistry of Phosphorus Wittig, Wittig-Horner and Wadsworth-Emmons reactions and their use in synthesis. Aza-Wittig reaction.Mitsunobu reaction, mechanism and applications.
  • Chemistry of Sulfur Introduction to organosulfur compounds (oxidation states, names etc.). Synthesis and chemistry of sulfoxides, allylic sulfoxide-sulfenic ester rearrangement. Pummerer reaction, syn elimination of sulfoxides.
  • Sulfone chemistry Julia reaction, Ramberg Backlund reaction and extrusion of SO2 from sulfolenes. Chemistry of sulfur ylids, Corey/Trost reagents.
  • Chemistry of Selenium Comparison of sulfur and selenium compounds. Reactions of selenoxides, syn elimination and [2,3] sigmatropic rearrangements. Oxidation reactions of selenium dioxide. Selenium mediated cyclisation reactions (PhSeCl etc.).

Teaching and Learning Strategies

Lectures

Worked examples

Material is presented via a series of lectures. Learning is supported via worked examples and ChemTube3D software.


Teaching Schedule
  Lectures Seminars Tutorials Lab Practicals Fieldwork Placement Other TOTAL
Study Hours 18

           18
Timetable (if known)              
Private Study 57
TOTAL HOURS 75

Assessment
EXAM Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
Unseen  2 hours  Semester 1  100  Yes  Standard UoL penalty applies  August resit opportunity for PGT students only where applicable. Integrated Master's students resit at the next normal opportunity.  
CONTINUOUS Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
             

Recommended Texts
  • Organic Chemistry, J. Clayden, N. Greeves, S. Warren and P. Wothers, OUP, 2nd edition 2012
  • "Organosulfur Chemistry" G.H Whitham, OUP, 1995
  • Selenium reagents and intermediates in organic synthesis, C. Paulmier, Pergamon
  • Asymmetric synthesis / edited by R. A. Aitken and S. N. Kilényi., Blackie Academic & Professional
  • Asymmetric synthesis, G. Procter, OUP
  • Principles of asymmetric synthesis, R.E. Gawley, Pergamon.
  • Asymmetric catalysis in organic synthesis, R. Noyori, Wiley, New York