Asymmetric Catalytic Enantio- and Diastereoselective Boron Conjugate Addition Reactions of α-Functionalized α,β-Unsaturated Carbonyl Substrates

Jian-Bo Xie*, Siqi Lin, Shuo Qiao and Guigen Li

*Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, United States, Email: nkjbxiegmail.com

J.-B. Xie, S. Lin, S. Qiao, G. Li, Org. Lett., 2016, 18, 3926-3929.

DOI: 10.1021/acs.orglett.6b01998

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Abstract

Cu[(S)-(R)-ppfa]Cl and AgNTf₂ as catalyst enable an asymmetric conjugate addition of B₂pin₂ onto α-functionalized α,β-unsaturated carbonyl compounds under mild, neutral conditions in the presence of an alcohol. AgNTf₂ and alcohols play crucial roles for achieving high catalytic activity and enantio- and diastereoselectivity.

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Key Words

benzyl boronates, alkyl boronates

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ID: J54-Y2016