Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes

Suman Chakrabarty, James M. Takacs

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.

Original languageEnglish (US)
Pages (from-to)6066-6069
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number17
DOIs
StatePublished - May 3 2017

ASJC Scopus subject areas

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

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