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Catalytic Asymmetric Synthesis of Optically Active Allenes from Terminal Alkynes

Juntao Ye, Suhua Li, Bo Chen, Wu Fan, Jinqiang Kuang, Jinxian Liu, Yu Liu, Bukeyan Miao, Baoqiang Wan, Yuli Wang, Xi Xie, Qiong Yu, Weiming Yuan and Shengming Ma*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China, Email:

J. Ye, S. Li, B. Chen, W. Fan, J. Kuang, J. Liu, Y. Liu, B. Miao, B. Wan, Y. Wang, X. Xie, Q. Yu, W. Yuan, S. Ma, Org. Lett., 2012, 14, 1346-1349.

DOI: 10.1021/ol300296k

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CuBr and ZnI2 catalyze an efficient asymmetric synthesis of axially chiral allenols with up to 97% ee from readily available propargylic alcohols, aliphatic or aromatic aldehyde, pyrrolidine, and commerically available ligands. The alcohol unit in the terminal alkynes plays a very important role for ensuring high enantioselectivity via coordination.

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proposed mechanism

One-Pot Synthesis of 1,3-Disubstituted Allenes from 1-Alkynes, Aldehydes, and Morpholine

J. Kuang, S. Ma, J. Am. Chem. Soc., 2010, 132, 1786-1787.

Key Words


ID: J54-Y2012-0710