CuH-Catalyzed Asymmetric Intramolecular Reductive Coupling of Allenes to Enones.

Org Lett

Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

Published: January 2018

The CuH-catalyzed asymmetric intramolecular reductive coupling of allenes to enones is successfully realized, providing cis-hydrobenzofurans with promising yields and excellent enantioselectivities. Such brilliant enantioselectivities are partially contributed by CuH-catalyzed favorable kinetic resolution of the cyclization products. This protocol tolerates a broad range of functional groups, allowing for further construction of tricyclic and bridged-ring structures. Moreover, the meta-chiral functionalization of 4-substituted phenol and asymmetric dearomatization modification of phenol-contained bioactive molecules are also described.

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http://dx.doi.org/10.1021/acs.orglett.7b03608DOI Listing

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