Catalytic asymmetric epoxidation of α,β-unsaturated esters using an yttrium-biphenyldiol complex

Hiroyuki Kakei; Riichiro Tsuji; Takashi Ohshima; Masakatsu Shibasaki

doi:10.1021/ja052466t

Catalytic asymmetric epoxidation of α,β-unsaturated esters using an yttrium-biphenyldiol complex

Hiroyuki Kakei, Riichiro Tsuji, Takashi Ohshima, Masakatsu Shibasaki

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

77 Citations (Scopus)

Abstract

We succeeded in a catalytic asymmetric epoxidation reaction of α,β-unsaturated esters via a conjugate addition of an oxidant using 2-10 mol % of the yttirium-chiral biphenyldiol catalyst. A variety of substrates with β-aryl and β-alkyl substituents were epoxidized efficiently, yielding the corresponding α,β-epoxy esters in up to 97% yield and 99% ee.

Original language	English
Pages (from-to)	8962-8963
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	25
DOIs	https://doi.org/10.1021/ja052466t
Publication status	Published - Jun 29 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja052466t

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abstract = "We succeeded in a catalytic asymmetric epoxidation reaction of α,β-unsaturated esters via a conjugate addition of an oxidant using 2-10 mol % of the yttirium-chiral biphenyldiol catalyst. A variety of substrates with β-aryl and β-alkyl substituents were epoxidized efficiently, yielding the corresponding α,β-epoxy esters in up to 97% yield and 99% ee.",

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AU - Kakei, Hiroyuki

AU - Tsuji, Riichiro

AU - Ohshima, Takashi

AU - Shibasaki, Masakatsu

PY - 2005/6/29

Y1 - 2005/6/29

N2 - We succeeded in a catalytic asymmetric epoxidation reaction of α,β-unsaturated esters via a conjugate addition of an oxidant using 2-10 mol % of the yttirium-chiral biphenyldiol catalyst. A variety of substrates with β-aryl and β-alkyl substituents were epoxidized efficiently, yielding the corresponding α,β-epoxy esters in up to 97% yield and 99% ee.

AB - We succeeded in a catalytic asymmetric epoxidation reaction of α,β-unsaturated esters via a conjugate addition of an oxidant using 2-10 mol % of the yttirium-chiral biphenyldiol catalyst. A variety of substrates with β-aryl and β-alkyl substituents were epoxidized efficiently, yielding the corresponding α,β-epoxy esters in up to 97% yield and 99% ee.

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ER -

Catalytic asymmetric epoxidation of α,β-unsaturated esters using an yttrium-biphenyldiol complex

Abstract

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