Catalytic Asymmetric Conjugate Addition of a Borylalkyl Copper Complex for Chiral Organoboronate Synthesis

Won Jun Jang, Jaesook Yun

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

We report the catalytic enantioselective conjugate addition of a borylalkyl copper nucleophile generated in situ from a 1,1-diborylmethane derivative to α,β-unsaturated diesters. In the presence of a chiral N-heterocyclic carbene (NHC)–copper catalyst, this method facilitated the enantioselective incorporation of a CH2Bpin moiety at the β-position of the diesters to yield β-chiral alkyl boronates in up to 86 % yield with high enantioselectivity. The alkylboron moiety in the resulting chiral diester products was converted into various functional groups by organic transformation of the C−B bond.

Original languageEnglish
Pages (from-to)18131-18135
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number50
DOIs
StatePublished - 9 Dec 2019

Bibliographical note

Funding Information:
This research was supported by National Research Foundation of Korea (NRF) grants (Nos.2019R1A2C2005706 and 2019R1A4A2001440) funded by the Korean government.

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • asymmetric catalysis
  • boron
  • conjugate addition
  • copper
  • diborylmethane

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