Name: Chandan Kumar Jana
M.S. degree: Indian Institute of Science, Bangalore, India
(2005)
Title: Desymmetrization of Cyclohexadienes and Its Application in Natural Product Synthesis


Homepage: www.uni-muenster.de/Chemie.oc/research/studer/group/jana.htm

Abstract of Research Project

The asymmetric allylation of carbonyl groups to produce chiral homoallylic alcohols is an important C-C bond forming reaction in organic synthesis. Metallated 1,4-cyclohexadiene, a bis-allylic system, is of particular interest since the six membered ring thus obtained has resident functionalities ready for further transformations. In the allylation using 1,4-cyclohexadiene, desymmetrization of the symmetric cyclohexadiene moiety can be achieved. Much effort has been put into the elaboration of asymmetric allylation of carbonyl groups but only very few of them have been devoted to the desymmetrization of cyclohexadienes. Recently, a new method (based on a Ti-TADDOL complex) for the desymmetrization of cyclohexadienes has been introduced by our group. However, to date no catalytic method of this desymmetrization has been developed. The goal of my planned thesis is the development of a catalytic desymmetrization reaction of 1,4-cyclohexadiene. In addition, the method should be applied in natural product synthesis.


Publications

C. K. Jana, A. Studer
Divergent Reactions on a Racemic Mixture: Catalytic Enantioselective Regiodivergent Nitroso Diels-Alder Reaction
Angew. Chem. Int. Ed. 46 (2007), 6542-6544.


Chandan Kumar Jana
eMail: Chandan Kumar Jana