Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by chiral ytterbium complexes

Ruifang Chen; Changtao Qian; Johannes G. de Vries

doi:10.1016/S0040-4039(01)01336-3

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by chiral ytterbium complexes

Ruifang Chen
, Changtao Qian
, Johannes G. de Vries

Stratingh Institute for Chemistry

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Abstract

Several derivatives of (S)-(−)-BINOL ligands with 6,6'-substitutents were synthesized and applied as chiral ligands in the Yb(O-i-Pr)3-catalyzed asymmetric epoxidation of α,β-unsaturated ketones. Superior results were obtained with 6,6'-diphenyl-BINOL, exemplified in the asymmetric epoxidation of (E)-1,3-diphenylprop-2-en-1-one in 91% yield and up to 97% ee.

Original language	English
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4039(01)01336-3
Publication status	Published - 2001

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title = "Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by chiral ytterbium complexes",

abstract = "Several derivatives of (S)-(−)-BINOL ligands with 6,6'-substitutents were synthesized and applied as chiral ligands in the Yb(O-i-Pr)3-catalyzed asymmetric epoxidation of α,β-unsaturated ketones. Superior results were obtained with 6,6'-diphenyl-BINOL, exemplified in the asymmetric epoxidation of (E)-1,3-diphenylprop-2-en-1-one in 91\% yield and up to 97\% ee.",

author = "Ruifang Chen and Changtao Qian and Vries, \{Johannes G. de\}",

note = "Relation: http://www.rug.nl/scheikunde/ date\_submitted:2006 Rights: University of Groningen. Stratingh Institute",

year = "2001",

doi = "10.1016/S0040-4039(01)01336-3",

language = "English",

volume = "42",

journal = "Tetrahedron Letters",

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T1 - Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by chiral ytterbium complexes

AU - Chen, Ruifang

AU - Qian, Changtao

AU - Vries, Johannes G. de

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2006 Rights: University of Groningen. Stratingh Institute

PY - 2001

Y1 - 2001

N2 - Several derivatives of (S)-(−)-BINOL ligands with 6,6'-substitutents were synthesized and applied as chiral ligands in the Yb(O-i-Pr)3-catalyzed asymmetric epoxidation of α,β-unsaturated ketones. Superior results were obtained with 6,6'-diphenyl-BINOL, exemplified in the asymmetric epoxidation of (E)-1,3-diphenylprop-2-en-1-one in 91% yield and up to 97% ee.

AB - Several derivatives of (S)-(−)-BINOL ligands with 6,6'-substitutents were synthesized and applied as chiral ligands in the Yb(O-i-Pr)3-catalyzed asymmetric epoxidation of α,β-unsaturated ketones. Superior results were obtained with 6,6'-diphenyl-BINOL, exemplified in the asymmetric epoxidation of (E)-1,3-diphenylprop-2-en-1-one in 91% yield and up to 97% ee.

U2 - 10.1016/S0040-4039(01)01336-3

DO - 10.1016/S0040-4039(01)01336-3

M3 - Article

VL - 42

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by chiral ytterbium complexes

Abstract

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