Download PDF
Synthesis 1993; 1993(5): 530-536
DOI: 10.1055/s-1993-25899
feature article
© 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.

Preparation of Functionalized Z-Olefins Using 1,1-Dimetalloalkanes

Charles E. Tucker* , Paul Knochel
  • *Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109, USA
Further Information

Publication History

Publication Date:
17 September 2002 (online)

 PDF Download  Permissions and Reprints All articles of this category

1,1-Dimetalloalkanes obtained by the allylzincation of alkenylmagnesium compounds react smoothly with various functionalized alkylidenemalonates providing functionalized Z-olefins in good yields. If dimenthyl alkylidenemalonates are used, then excellent stereoselectivities are observed (92:8 to 100:0). An application to a short stereospecific synthesis of an insect pheromone [(Z)-7-dodecenyl acetate] is described (> 99.9% Z, 70% overall yield).