A Stereoselective Reductive Hosomi-Sakurai Reaction.

Org Lett

Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.

Published: March 2018

A novel reductive variant of the classical Hosomi-Sakurai reaction is reported. This transformation hinges on a redox-neutral, stereoselective internal reduction event under mild conditions. This operationally simple reaction relies on readily available starting materials and leads to useful products in diastereoselectivities of up to 7:1. The versatility of this new method is demonstrated through the stereoselective one-step synthesis of an AChE inhibitor.

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http://dx.doi.org/10.1021/acs.orglett.8b00276DOI Listing

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