Indium-mediated Barbier-type allylation of aldehydes as a convenient method for the highly enantioselective synthesis of homoallylic alcohols

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• 作者：Hirayama ; Lacie C. ; Gamsey ; Soya ; Knueppel ; Daniel ; Steiner ; Derek ; DeLaTorre ; Kelly ; Singaram ; Bakthan
• 关键词：Indium ; Allylation ; Amino alcohol ; Homoallylic alcohol ; Asymmetric
• 刊名：Tetrahedron Letters
• 出版年：2005
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：March 28, 2005
• 卷：46
• 期：13
• 页码：2315-2318
• 文件大小：110 K

摘要

We report a general method for the indium-mediated Barbier-type enantioselective allylation of both aromatic and aliphatic aldehydes using commercially available (1S,2R)-(+)-2-amino-1,2-diphenylethanol as a chiral auxiliary. Using only two equivalents of allyl bromide, excellent yields and very good to excellent enantioselectivities are obtained. To our knowledge, the enantioselectivities reported herein are the highest obtained for indium-promoted allylations of carbonyl compounds.