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Keywords:

  • Cyclopropanation;
  • Organocatalysis;
  • Enantioselectivity;
  • Diastereoselectivity;
  • Quaternary centers

Abstract

A convenient and novel domino reaction for the synthesis of highly functionalized cyclopropanes is reported. The addition of 2-bromoketo esters to a variety of α,β-unsaturated aldehydes catalyzed by secondary amines leads to chiral cyclopropanes with three stereogenic carbon atoms, including one quaternary stereocenter, in a highly stereocontrolled fashion.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)