PDF herunterladen
Synlett 1995; 1995(12): 1197-1207
DOI: 10.1055/s-1995-5231
account
© 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.

The Asymmetric Cyclopropanation of Acyclic Allylic Alcohols: Efficient Stereocontrol with Iodomethylzinc Reagents

André B. Charette* , Jean-François Marcoux
  • *Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7, Fax (514) 343-5900; e-mail: charetta@ERE.UMontreal.CA
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

The asymmetric cyclopropanation of acyclic allylic alcohols can now be achieved with unprecedently high level of stereocontrol with halomethylzinc reagents. The ability of proximal basic groups to ”deliver” the methylene unit to a nearby olefin has been used to develop efficient reaction conditions for the cyclopropanation of allylic alcohols. This property was employed to improve the diastereoselection observed in the cyclopropanation of chiral, acyclic allylic alcohols; in the development of an efficient chiral auxiliary; and finally in the design of an efficient stoichiometric chiral reagent for the cyclopropanation of allylic alcohols.

cyclopropanation - chiral auxiliaries - organozinc - carbenoids - allylic alcohols