Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol

Colton R. Davis, Irungu K. Luvaga, Joseph M. Ready

Research output: Contribution to journalArticlepeer-review

Abstract

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

Original languageEnglish (US)
Pages (from-to)4921-4927
Number of pages7
JournalJournal of the American Chemical Society
Volume143
Issue number13
DOIs
StatePublished - Apr 7 2021

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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