Download PDF
Synlett 1990; 1990(11): 701-703
DOI: 10.1055/s-1990-21217
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.

Diastereoselective Heteroconjugate Addition Using Phenylthioacetylene

Angkana Herunsalee* , Minoru Isobe, Yoshio Fukuda, Toshio Goto
  • *Laboratory of Organic Chemistry, School of Agriculture, Nagoya University, Chikusa, Nagoya 464, Japan
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Phenylthioacetylene, as its lithium acetylide, was used for the opening of epoxides to afford 1-phenylthio-1-alkyn-4-ols. Hydrosilylation of the acetylene moiety was followed by oxidation of sulfur to give the corresponding 4-hydroxy-1-silyl-1-alkenyl sulfones, which act as the electrophile in heteroconjugate addition. Very high stereoselectivity is shown in the addition. The stereocontrolled processes are discussed.

      >