Journal
TETRAHEDRON LETTERS
Volume 48, Issue 48, Pages 8424-8429Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.09.172
Keywords
cyclopropanols; titanacyclopropanes; cyclopropyl-allyl rearrangement; allyl bromides; trisubstituted olefins; stereoselectivity
Categories
Ask authors/readers for more resources
Methanesulfonates of readily available cis-1,2-disubstituted cyclopropanols on reaction with magnesium bromide in diethyl ether undergo cyclopropyl-allyl rearrangement to afford ally] bromides, with an (E)-trisubstituted double bond, as main products. The amount of the corresponding (Z)-isomers did not exceed 5% when the reaction was performed at 0 degrees C, and the major concomitant products were the regioisomeric secondary bromides. The latter are sufficiently less reactive towards sulfur, phosphorus and hydrogen nucleophiles than the dominant (E -disubstituted allyl bromides and these reactions are suitable for the stereoselective preparation of trisubstituted olefins. (c) 2007 Published by Elsevier Ltd.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available