4.8 Article

Catalytic Asymmetric oxa-Michael-Michael Cascade for Facile Construction of Chiral Chromans via an Aminal Intermediate

Journal

ORGANIC LETTERS
Volume 11, Issue 7, Pages 1627-1630

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol9003433

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Funding

  1. National Science foundation [CHE-0704015]
  2. NSF CRIPMU award to the University of New Mexico [CHE-0443580]

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An unprecedented highly enantioselective cascade oxa-Michael-Michael reaction has been developed. The simple and practical process, efficiently catalyzed by chiral diphenylprolinol TMS ether, affords a powerful access to highly functionalized synthetically useful chiral chromans. Moreover, notably a new activation mode involving an aminal is disclosed for the first time.

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