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Asymmetric Synthesis of γ-Hydroxy Pinacolboronates through Copper-Catalyzed Enantioselective Hydroboration of α,β-Unsaturated Aldehydes

Won Jun Jang, Seung Min Song, Yeji Park, Jaesook Yun*

*Department of Chemistry, Sungkyunkwan University, Suwon 16419, Korea, Email: jaesookskku.edu

W. J. Jang, S. M. Song, Y. Park, J. Yun, J. Org. Chem., 2019, 84, 4429-4434.

DOI: 10.1021/acs.joc.8b03045 (free Supporting Information)



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Abstract

A copper-catalyzed enantioselective hydroboration of α,β-unsaturated aldehydes with pinacolborane provides the corresponding γ-pinacolboronate alcohols in good yields and enantioselectivities through consecutive hydroboration of the C=O and C=C bonds. The resulting γ-pinacolboronate alcohols could be utilized in various transformations.

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Key Words

benzyl boronates, pinacolborane


ID: J42-Y2019