Chiral allene-containing phosphines in asymmetric catalysis

Feng Cai; Xiaotao Pu; Xiangbing Qi; Vincent Lynch; Akella Radha; Joseph M. Ready

doi:10.1021/ja207748r

Chiral allene-containing phosphines in asymmetric catalysis

Feng Cai, Xiaotao Pu, Xiangbing Qi, Vincent Lynch, Akella Radha, Joseph M. Ready

Research output: Contribution to journal › Article › peer-review

110 Scopus citations

Abstract

We demonstrate that allenes, chiral 1,2-dienes, appended with basic functionality can serve as ligands for transition metals. We describe an allene-containing bisphosphine that, when coordinated to Rh(I), promotes the asymmetric addition of arylboronic acids to α-keto esters with high enantioselectivity. Solution and solid-state structural analysis reveals that one olefin of the allene can coordinate to transition metals, generating bi- and tridentate ligands.

Original language	English (US)
Pages (from-to)	18066-18069
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	45
DOIs	https://doi.org/10.1021/ja207748r
State	Published - Nov 16 2011

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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T1 - Chiral allene-containing phosphines in asymmetric catalysis

AU - Cai, Feng

AU - Pu, Xiaotao

AU - Qi, Xiangbing

AU - Lynch, Vincent

AU - Radha, Akella

AU - Ready, Joseph M.

PY - 2011/11/16

Y1 - 2011/11/16

N2 - We demonstrate that allenes, chiral 1,2-dienes, appended with basic functionality can serve as ligands for transition metals. We describe an allene-containing bisphosphine that, when coordinated to Rh(I), promotes the asymmetric addition of arylboronic acids to α-keto esters with high enantioselectivity. Solution and solid-state structural analysis reveals that one olefin of the allene can coordinate to transition metals, generating bi- and tridentate ligands.

AB - We demonstrate that allenes, chiral 1,2-dienes, appended with basic functionality can serve as ligands for transition metals. We describe an allene-containing bisphosphine that, when coordinated to Rh(I), promotes the asymmetric addition of arylboronic acids to α-keto esters with high enantioselectivity. Solution and solid-state structural analysis reveals that one olefin of the allene can coordinate to transition metals, generating bi- and tridentate ligands.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 45

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Chiral allene-containing phosphines in asymmetric catalysis

Abstract

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