Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species

Won Jun Jang, Jeongkyu Woo, Jaesook Yun

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12 Scopus citations

Abstract

We report the diastereo- and enantioselective conjugate addition of chiral secondary borylalkyl copper species derived from borylalkenes in situ to α,β-unsaturated diesters. In the presence of a chiral bisphosphine-ligated CuH catalyst, the conjugate addition provides a direct access to enantioenriched alkylboron compounds containing two contiguous carbon stereogenic centers in good yield with high diastereo- and enantioselectivity (up to >98:2 dr, >99:1 er) by assembling readily available starting alkenyl reagents in a single operation without using preformed organometallic reagents or chiral auxiliaries. The resulting products were used in various organic transformations. The utility of the synthetic approach was highlighted by the synthesis of (−)-phaseolinic acid.

Original languageEnglish
Pages (from-to)4614-4618
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number9
DOIs
StatePublished - 23 Feb 2021

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Keywords

  • asymmetric catalysis
  • borylalkene
  • conjugate addition
  • copper
  • enantioselective synthesis

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