Enantioselective Cyclopropanation of Allylic Alcohols with Dioxaborolane Ligands:  Scope and Synthetic Applications

A very effective chiral controller has been found for the conversion of allylic alcohols into the corresponding enantiomerically enriched cyclopropanes using bis(iodomethyl)zinc. A variety of chiral, nonracemic cyclopropylmethanols could be obtained according to this method. This methodology was ext...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1998-11, Vol.120 (46), p.11943-11952
Main Authors: Charette, André B, Juteau, Hélène, Lebel, Hélène, Molinaro, Carmela
Format: Article
Language:English
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Summary:A very effective chiral controller has been found for the conversion of allylic alcohols into the corresponding enantiomerically enriched cyclopropanes using bis(iodomethyl)zinc. A variety of chiral, nonracemic cyclopropylmethanols could be obtained according to this method. This methodology was extended with success to the cyclopropanation of unconjugated and conjugated polyenes and homoallylic alcohols. The cyclopropanation of allylic carbamates has also been investigated with this system, but it was found that enantioenriched cyclopropylmethylamines are best prepared from enantioenriched cyclopropylmethanols.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja982055v