Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes

Veronika M. Shoba, James M. Takacs

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Oxime-directed catalytic asymmetric hydroboration is diverted to catalytic asymmetric hydrogenation (CAH) upon the addition of a proton source, such as MeOH, or by running the reaction under a hydrogen atmosphere. A borane (e.g., pinacolborane) is required to promote CAH. Tri- and tetrasubstituted alkenes, including the challenging all-alkyl tetrasubstituted alkenes, undergo CAH with enantiomer ratios (er) as high as 99:1. The mild reaction conditions, i.e., ambient temperature, moderate reaction times, and the need for only a slight excess of H2, contrast those used in most state-of-the-art catalysts for related substrates.

Original languageEnglish (US)
Pages (from-to)5740-5743
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number16
DOIs
StatePublished - Apr 26 2017

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes'. Together they form a unique fingerprint.

Cite this