Catalytic asymmetric synthesis of optically active allenes from terminal alkynes.

Org Lett

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.

Published: March 2012

CuBr and ZnI(2) have been developed as catalysts or subcatalysts for the 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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http://dx.doi.org/10.1021/ol300296kDOI Listing

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