PDF herunterladen
Synlett 1997; 1997(SI): 449-450
DOI: 10.1055/s-1997-6144
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.

Stereoselective Conjugate Addition of an α-Sulfinyl Carbanion to α,β-Unsaturated Esters: Asymmetric Synthesis of Cycloalkanecarboxylates

Takeshi Toru* , Shuichi Nakamura, Hirofumi Takemoto, Yoshio Ueno
  • *Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466, Japan, Fax 52-735-5247; E-mail toru@ach.nitechn.ac.jp
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

The reaction of lithiated (R)-2-(trimethylsilyl)ethyl p-tolyl sulfoxide 1 with α,β-unsaturated esters gives 1,4-conjugate addition products as single stereoisomers, whereas the reaction of 1 with 4-, 6-, or 7-haloalkenoates affords cyclopropane-, cyclopentane- or cyclohexanecarboxylates, respectively, with high stereoselectivity.

α-sulfinyl carbanion - chiral sulfoxide - conjugate addition - chiral cycloalkanes