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

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13 Scopus citations

Abstract

We report a copper-catalyzed enantioselective hydroboration of α,β-unsaturated aldehydes with pinacolborane. α,β-Unsaturated aldehydes were converted to the corresponding γ-pinacolboronate alcohols in good yields and enantioselectivities through consecutive hydroboration of the C=O and C=C bonds. This process provides simple access to the hydroborated product of allylic alcohols, and the resulting γ-pinacolboronate alcohols could be utilized in various transformations.

Original languageEnglish
Pages (from-to)4429-4434
Number of pages6
JournalJournal of Organic Chemistry
Volume84
Issue number7
DOIs
StatePublished - 5 Apr 2019

Bibliographical note

Funding Information:
This research was supported by a National Research Foundation of Korea grant (NRF-2016R1A2B4011719), funded by the Korean government (MEST).

Publisher Copyright:
© 2019 American Chemical Society.

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