Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling

Gia L. Hoang, James M. Takacs

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

The rhodium-catalyzed, directed catalytic asymmetric hydroboration of γ,δ-unsaturated amides affords a direct route to chiral acyclic secondary γ-borylated carbonyl derivatives in high enantiomeric purity. In contrast to a similar β-borylated amide derivative, the γ-borylated amide undergoes Suzuki-Miyaura cross-coupling with stereoretention. The utility of the boronic ester products is further illustrated by other stereospecific C-B bond transformations leading to γ-amino acid derivatives, 1,4-amino alcohols, and 5-substituted-γ-lactone and γ-lactam ring systems.

Original languageEnglish (US)
Pages (from-to)4511-4516
Number of pages6
JournalChemical Science
Volume8
Issue number6
DOIs
StatePublished - Jan 1 2017

ASJC Scopus subject areas

  • Chemistry(all)

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