Development of Non-C2-symmetric ProPhenol Ligands. The Asymmetric Vinylation of N-Boc Imines

Barry M. Trost*, Chao-I (Joey) Hung, Dennis C. Koester and Yan Miller

*Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States, Email: bmtroststanford.edu

B. M. Trost, C.-I Hung, D. C. Koester, Y. Miller, Org. Lett., 2015, 17, 3778-3781.

DOI: 10.1021/acs.orglett.5b01755

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Abstract

The use of a non-C2-symmetric ProPhenol ligands enables a catalytic and asymmetric vinylation of N-Boc imines via hydrozirconation providing allylic amines in excellent yields and enantioselectivities. A very short, asymmetric synthesis of the selective serotonine reuptake inhibitor (SSRI) (-)-dapoxetine is also reported.

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Key Words

allylic amines, Schwartz's reagent

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ID: J54-Y2015