1242409-13-7Relevant academic research and scientific papers
Organocatalyzed cyclopropanation of α-substituted α,β-unsaturated aldehydes: Enantioselective synthesis of cyclopropanes bearing a chiral quaternary center
Terrasson, Vincent,Van Der Lee, Arie,De Figueiredo, Renata Mareia,Campagne, Jean Marc
supporting information; experimental part, p. 7875 - 7880 (2010/09/18)
An enantioselective cyclopropanation of α-substituted α,β-unsaturated aldehydes with bromomalonate has been successfully developed through a domino Michael/a-alkylation strategy. The method allows the efficient formation of cyclopropanes bearing a quaternary carbon stereocenter at the a-position of the aldehydes by using iminium/enamine catalysis and gives a nice extension on the organocatalytic cyclopropanation of bromomalonate and α β-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. 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim aldehydes, cyclopropanes, domino reactions, organocatalysis, quaternary stereocenters.
