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Title: Organocatalyzed cyclopropanation of alpha-substituted alpha,beta-unsaturated aldehydes: enantioselective synthesis of cyclopropanes bearing a chiral quaternary center. Author: Terrasson V, van der Lee A, de Figueiredo RM, Campagne JM. Journal: Chemistry; 2010 Jul 12; 16(26):7875-80. PubMed ID: 20512823. Abstract: An enantioselective cyclopropanation of alpha-substituted alpha,beta-unsaturated aldehydes with bromomalonate has been successfully developed through a domino Michael/alpha-alkylation strategy. The method allows the efficient formation of cyclopropanes bearing a quaternary carbon stereocenter at the alpha-position of the aldehydes by using iminium/enamine catalysis and gives a nice extension on the organocatalytic cyclopropanation of bromomalonate and alpha,beta-unsaturated aldehydes previously reported by other groups. Very good yields (up to 81%) and enantioselectivities (up to 97% ee) have been obtained. The optically active cyclopropane derivatives are of high synthetic interest as useful targets for further elaboration into more complex structures.[Abstract] [Full Text] [Related] [New Search]