Download PDF
Synlett 1993; 1993(1): 29-31
DOI: 10.1055/s-1993-22335
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.

[3+1] Synthetic Route Toward Synthesis of Cyclobutane/butene Derivatives Based on the Large α-Cation-Stabilizing Effect of Cyclopropane1

Tetsuya Nagasawa* , Keisuke Suzuki
  • *Department of Chemistry, Keio University, Hiyoshi, Yokohama 223, Japan
Further Information

Publication History

Publication Date:
19 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The large α-cation-stabilizing effect of cyclopropyl group was utilized in the efficient two-step synthesis of cyclobutane and cyclobutene derivatives:The first step is the Lewis acid-promoted carbonyl ene reaction, where vinylcyclopropane 2 acts as a particularly efficient ene donor to give alcohol 3 in high yield. Treatment of this ene adduct 3 with triflic anhydride in the presence of collidine led to the formation of cyclobutane derivatives in high yield. Furthermore, we found that treatment of the reaction mixture of the triflate formation with Et3N cleanly effected elimination of the triflic acid to give cyclobutene in high yield.

      >