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 journalArticle

55 Citations (Scopus)

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

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hydroboration
Phosphites
Rhodium
rhodium
Styrenes
Bearings (structural)
Electrons
Enantioselectivity
styrenes
Chlorides
electrons
chlorides
Ligands
catalysts
ligands
Catalysts
phosphoramidite
4,4,5,5-tetramethyl(1,3,2)dioxaborolane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration. / Moteki, Shin A.; Wu, Di; Chandra, Kusum L.; Sahadeva Reddy, D.; Takacs, James M.

In: Organic Letters, Vol. 8, No. 14, 06.07.2006, p. 3097-3100.

Research output: Contribution to journalArticle

Moteki, Shin A. ; Wu, Di ; Chandra, Kusum L. ; Sahadeva Reddy, D. ; Takacs, James M. / TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration. In: Organic Letters. 2006 ; Vol. 8, No. 14. pp. 3097-3100.
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AU - Takacs, James M

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