Download PDF
Synthesis 1992; 1992(1/2): 127-131
DOI: 10.1055/s-1992-34179
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Complementary Facial Selectivity in Conjugate Additions to γ-Hydroxyenones

Kevin A. Swiss* , William Hinkley, Cynthia A. Maryanoff, Dennis C. Liotta
  • *Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA
Further Information

Publication History

Publication Date:
18 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Complementary facial selectivity can be achieved in conjugate additions to γ-hydroxyenones by using either Grignard reagents or cuprates. In the case of the former, preliminary complexation of the magnesium reagent with the resident alkoxide, followed by alkyl group transfer, results in the exclusive formation of the syn product. Conversely, cuprate conjugate additions proceed in an anti fashion, presumably because, in this mode of addition, coulombic repulsions are minimized.