Enantioselective Cyclopropanation of Allylic Alcohols with Dioxaborolane Ligands: Scope and Synthetic Applications
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- 作者：André ; B. Charette ; Hé ; lè ; ne Juteau ; Hé ; lè ; ne Lebel ; and Carmela Molinaro
- 刊名：Journal of the American Chemical Society
- 出版年：1998
- 出版时间：November 25, 1998
- 年：1998
- 卷：120
- 期：46
- 页码：11943 - 11952
- 全文大小：264K
- 年卷期：v.120,no.46(November 25, 1998)
- ISSN：1520-5126
文摘
A very effective chiral controller has been found for the conversion of allylic alcohols into thecorresponding enantiomerically enriched cyclopropanes using bis(iodomethyl)zinc. A variety of chiral,nonracemic cyclopropylmethanols could be obtained according to this method. This methodology was extendedwith success to the cyclopropanation of unconjugated and conjugated polyenes and homoallylic alcohols. Thecyclopropanation of allylic carbamates has also been investigated with this system, but it was found thatenantioenriched cyclopropylmethylamines are best prepared from enantioenriched cyclopropylmethanols.