CY 6123 : Asymmetric Organic synthesis

Course Objectives: Learn various asymmetric transformations and employ such reactions in asymmetric organic synthesis of important chiral molecules.

Learning Outcome: At the end of the course, the learners should be able to:

Apply asymmetric transformations in a logical manner for the synthesis of chiral molecules.

Course Contents:

Stereoselective reactions: Classification, importance and advantages; diastereoselective reactions.

Asymmetric synthesis: Importance, classification and principle; modes of asymmetric induction

Metal catalyzed asymmetric enantioselective oxidation, reduction, C-C bond forming reactions, allylic substitution, cyclization, and other important reactions.

Chiral organocatalysts including phase transfer catalysts and hydrogen-bonding catalysts, and supported chiral catalysts.

Kinetic resolution, parallel kinetic resolution, dynamic kinetic resolution and dynamic thermodynamic resolution.

Chiral poisoning, chiral activation, desymmetrization, nonlinear effect, autocatalysis, auto induction, double diastereoselection and remote chiral induction in asymmetric synthesis

Determination of optical purity using NMR, GC and HPLC techniques including principles, determination of absolute configuration by NMR and X-Ray crystallography.

Application of asymmetric synthesis in the industrially relevant molecules such as L-DOPA, (S)-metolachlor, carbapenem and menthol.

Text Books:

  1. Stereoselectivity in organic synthesis, G. Procter, Oxford Chemistry Primers, 2007.
  2. Fundamentals of asymmetric catalysis, P.J.Walsh and M.C. Kozlowski, University science books, USA, 2009.
  3. Catalytic Asymmetric Synthesis, 3rd ed,Ed: I. Ojima, John Wiley & Sons, New Jersey, 2010.
  4. Comprehensive Asymmetric Catalysis I-III; Editors: Eric N. Jacobsen, Andreas Pfaltz, Hisashi Yamamoto; Springer-Verlag Berlin Heidelberg, Germany, 1999.
  5. Asymmetric Synthesis – The Essentials, Eds.: M. Christmann and S. Brase, Wiley-VCH Verlag GmbH, Weinheim, 2007.