TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration

Shin A. Moteki, Di Wu, Kusum L. Chandra, D. Sahadeva Reddy, James M. Takacs

Research output: Contribution to journalArticlepeer-review

56 Scopus citations

Abstract

Two simple TADDOL-derived monodentate ligands, the (1R,2S)-2- phenylcyclohexanol-derived phosphite and the N,N-(phenylbenzyl)-phosphoramidite, give comparably high levels of enantioselectivity (90-96% ee) in the rhodium-catalyzed hydroborations of substituted styrenes bearing either electron-donating or electron-withdrawing substituents. Rhodium(I) chloride and tetrafluoroborate catalyst precursors give comparable results. Pinacolborane is superior to catecholborane in these reactions.

Original languageEnglish (US)
Pages (from-to)3097-3100
Number of pages4
JournalOrganic Letters
Volume8
Issue number14
DOIs
StatePublished - Jul 6 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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