Allenes in asymmetric catalysis: Asymmetric ring opening of meso-epoxides catalyzed by allene-containing phosphine oxides

Xiaotao Pu, Xiangbing Qi, Joseph M. Ready

Research output: Contribution to journalArticle

75 Citations (Scopus)

Abstract

(Chemical Equation Presented) Unsymmetrically substituted allenes (1,2-dienes) are inherently chiral and can be prepared in optically pure form. Nonetheless, to date the allene framework has not been incorporated into ligands for asymmetric catalysis. Since allenes project functionality differently than either tetrahedral carbon or chiral biaryls, they may create complementary chiral environments. This study demonstrates that optically active, C 2-symmetric allene-containing bisphosphine oxides can catalyze the addition of SiCl4 to meso-epoxides with high enantioselectivity. The epoxide opening likely involves generation of a Lewis acidic, cationic (bisphosphine oxide)SiCl3 complex. The fact that high asymmetric induction is observed suggests that allenes may represent a new platform for the development of ligands and catalysts for asymmetric synthesis.

Original languageEnglish (US)
Pages (from-to)10364-10365
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number30
DOIs
StatePublished - Aug 5 2009

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phosphine
Epoxy Compounds
Catalysis
Oxides
Ligands
Enantioselectivity
Catalysts
Carbon
propadiene

ASJC Scopus subject areas

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

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Allenes in asymmetric catalysis : Asymmetric ring opening of meso-epoxides catalyzed by allene-containing phosphine oxides. / Pu, Xiaotao; Qi, Xiangbing; Ready, Joseph M.

In: Journal of the American Chemical Society, Vol. 131, No. 30, 05.08.2009, p. 10364-10365.

Research output: Contribution to journalArticle

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