Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling

Gia L. Hoang, Zhao Di Yang, Sean M. Smith, Rhitankar Pal, Judy L. Miska, Damaris E. Pérez, Libbie S.W. Pelter, Xiao Cheng Zeng, James M. Takacs

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

Original languageEnglish (US)
Pages (from-to)940-943
Number of pages4
JournalOrganic Letters
Volume17
Issue number4
DOIs
StatePublished - Feb 20 2015

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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