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Highly Stereoselective Facile Synthesis of 2-Acetoxy-1,3(E)-alkadienes via a Rh(I)-Catalyzed Isomerization of 2,3-Allenyl Carboxylates

Xiaobing Zhang, Chunling Fu, and Shengming Ma*

*Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People’s Republic of China, Email: masmsioc.ac.cn

X. Zhang, C. Fu, S. Ma, Org. Lett., 2011, 13, 1920-1923.

DOI: 10.1021/ol200198z (free Supporting Information)


Abstract

A highly stereoselective Rh(I)-catalyzed 1,3-acetoxyl rearrangement of 1,2-allen-3-yl carboxylates leads to 2-acetoxy-1,3(E)-alkadienes. Features of the reaction are a high catalytic efficiency, broad scope and excellent E-selectivity.

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Key Words

1,3-Dienes, Enols


ID: J54-Y2011-0990