ORGN 191 |
| A water soluble cavitand has been used to control the stereoselectivity of electrocyclization reactions. A chiral molecule which is either bound to the photo-substrate or present in the same cavity of the substrate acts as the inductor. Formation of the 2:1 host : guest complex has been analyzed by NMR studies. NOE interactions between the host, substrate and chiral inductor / auxiliary have been used to ascertain the mode of binding. While the reaction is racemic in the absence of the chiral group or the host molecule, in presence of both these groups, stereoselective reactions are observed. Different examples were studied to understand the role of the host molecule and the chiral auxiliary in this reaction. The observed selectivity is better explained as a coaction of the chiral moiety and the host cavitand.
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Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster
Sci-Mix
Division of Organic Chemistry |
