Regio- and stereoselective cyclopropanation of functionalised dienes. Novel methodology for the synthesis of vinyl- and divinyl-cyclopropanes

Dienes, bearing an electron-withdrawing substituent at C-1, are cyclopropanated regio- and stereoselectively at the CC double bond proximal to this electron-withdrawing group. The highest selectivity is observed in the case of dienylboronates. The cyclopropanation of these substrates affords almost...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2002-03, Vol.43 (12), p.2317-2320
Main Authors: Markó, István E., Giard, Thierry, Sumida, Shinichi, Gies, Anne-Elisabeth
Format: Article
Language:English
Subjects:
cyclopropanes
dienylboronates
palladium
Suzuki coupling
vinylcyclopropanes
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Dienes, bearing an electron-withdrawing substituent at C-1, are cyclopropanated regio- and stereoselectively at the CC double bond proximal to this electron-withdrawing group. The highest selectivity is observed in the case of dienylboronates. The cyclopropanation of these substrates affords almost exclusively the synthetically useful 1-boronato-2-vinyl-cyclopropanes. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)00242-3