Download PDF
Synlett 1994; 1994(5): 351-352
DOI: 10.1055/s-1994-22851
letter
© 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.

Enantiocontrolled Conjugate Addition of Chiral Alkoxydimethylcuprate to Macrocyclic Enones

K. Tanaka* , J. Matsui, K. Somemiya, H. Suzuki
  • *Department of Chemistry, Faculty of Science, Kyoto University, Kitashirakawa, Sakyo, Kyoto 606, Japan
Further Information

Publication History

Publication Date:
22 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The asymmetric conjugate addition reactions of the chiral organocuprate, prepared from (1R, 2R, 3S, 4S)-3-[(1-methyl-pyrrol-2-yl) methylamino]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (1) with ten-to eighteen-membered ring enones afforded chiral cyclic ketones in 52-99% enantiomeric excess (ee). The conjugate addition to (Z)-cycloalkenones (C10 and C11) gave the S-configuration of chiral 3-methylketones, whereas the reaction with (E)-cycloalkenones (C11, C12, C13, C14, C15, C16, and C17) gave (R)-ketones.