We have recently reported an enantioselective chlorolactonization method for 4-substituted-4-pentenoic acids.  The optimized conditions for this reaction use (DHQD)2PHAL as a catalyst and chlorinated hydantoins as a chlorine source delivering the desired chlorolactones with good conversions and high enantioselectivities.  One current area of attention is the mechanism of the reaction; which we believe is the formation of an active complex between the chlorinated hydantoin and (DHQD)2PHAL.   In efforts to both probe the mechanism and search for improved catalyst structures, we have turned to structure enantioselectivity relationship studies involving derivatives of cinchona alkaloid dimers. 

Structure enantioselectivity relationship studies involving cinchona alkaloid dimers for the the stereoselective organocatalytic chlorolactonization

240th National Meeting (2010)

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