Synlett 1997; 1997(8): 977-979
DOI: 10.1055/s-1997-5790
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 Synthesis of Cyclopropyl Boronic Esters

Jörg Pietruszka* , Markus Widenmeyer
  • *Institut für Organische Chemie und Isotopenforschung, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax: +711 685 4321; E-mail: [email protected]
Further Information

Publication History

Publication Date:
31 December 2000 (online)

The conversion of simple 1-alkynes to optically active 2-alkyl-cyclopropan-1-ols is conveniently achieved by a simple protocol. The key step is the cyclopropanation of alkenyl boronic esters derived from (+)-diisopropyl L-tartrate and alkenyl boronic acids. It has been found that best yields could be obtained using diazomethane and palladium(II) acetate as catalyst. The systematic investigation of parameters influencing this reaction led to an improvement of the diastereoselectivity of the transformation.