Copper-Catalyzed Tandem Hydrocupration and Diastereo- and Enantioselective Borylalkyl Addition to Aldehydes

Won Jun Jang, Jaesook Yun

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

We report the copper-catalyzed stereoselective addition of in situ generated chiral boron-α-alkyl intermediates to various aldehydes including α,β-unsaturated aldehydes under mild conditions. This tandem and multicomponent method facilitated the synthesis of enantiomerically enriched 1,2-hydroxyboronates bearing contiguous stereocenters in good yield with high diastereo- and enantioselectivity up to a ratio greater than 98:2. In particular, α,β-unsaturated aldehydes were successfully used as electrophiles in Cu−H catalysis through 1,2-addition without significant reduction. The resulting 1,2-hydroxyboronates were used in various transformations.

Original languageEnglish
Pages (from-to)12116-12120
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number37
DOIs
StatePublished - 10 Sep 2018

Bibliographical note

Funding Information:
This research was supported by National Research Foundation of Korea (NRF) grants (NRF-2016R1A2B4011719 and NRF-2016R1A4A1011451), funded by the Korean government (MEST).

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • aldehyde addition
  • asymmetric catalysis
  • enantioselective synthesis
  • homogeneous catalysis
  • vinylboronate

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