Tetrahedron

Studies on Cu (I)-catalyzed synthesis of simple 3-substituted 1, 2-allenes and optically active 2-substituted secondary 2, 3-allenols

J Li, C Zhou, C Fu, S Ma

Index: Li, Jing; Zhou, Chao; Fu, Chunling; Ma, Shengming Tetrahedron, 2009 , vol. 65, # 18 p. 3695 - 3703

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Citation Number: 10

Abstract

The sequential treatment of terminal alkynes or propargylic alcohols with n-BuLi and MOMCl afforded the corresponding propargylic methyl ethers, which would react with primary alkyl Grignard reagents under the catalysis of CuBr to afford 3-substituted 1, 2-allenes or 2- substituted secondary 2, 3-allenols, respectively. The reaction may be applied to the synthesis of optically active 2-substituted secondary 2, 3-allenols with up to> 99% ee ...