Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes

Ryo Irie; Keiko Noda; Yoshio Ito; Tsutomu Katsuki

doi:10.1016/S0040-4039(00)74486-8

Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes

Ryo Irie, Keiko Noda, Yoshio Ito, Tsutomu Katsuki

Organic and Biological Chemistry

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156 Citations (Scopus)

Abstract

Chiral (salen)manganese(III) complexes (3 and 4) were prepared and used for the enantioselective epoxidation of unfunctionalized olfefins. The highest enantioselectivity of 48% ee for the catalytic epoxidation of (E)-stilbene was realized by using 3 as a catalyst though much lower enantioselectivity (7% ee) was obtained for that of (E)-1-phenyl-1-propene. In the epoxidation of (Z)-olefins, enantioselectivities were in the range of 68-72% ee by using 3 as a catalyst and 60% ee by using 4.

Original language	English
Pages (from-to)	1055-1058
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(00)74486-8
Publication status	Published - Feb 18 1991

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes",

abstract = "Chiral (salen)manganese(III) complexes (3 and 4) were prepared and used for the enantioselective epoxidation of unfunctionalized olfefins. The highest enantioselectivity of 48% ee for the catalytic epoxidation of (E)-stilbene was realized by using 3 as a catalyst though much lower enantioselectivity (7% ee) was obtained for that of (E)-1-phenyl-1-propene. In the epoxidation of (Z)-olefins, enantioselectivities were in the range of 68-72% ee by using 3 as a catalyst and 60% ee by using 4.",

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T1 - Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes

AU - Irie, Ryo

AU - Noda, Keiko

AU - Ito, Yoshio

AU - Katsuki, Tsutomu

PY - 1991/2/18

Y1 - 1991/2/18

N2 - Chiral (salen)manganese(III) complexes (3 and 4) were prepared and used for the enantioselective epoxidation of unfunctionalized olfefins. The highest enantioselectivity of 48% ee for the catalytic epoxidation of (E)-stilbene was realized by using 3 as a catalyst though much lower enantioselectivity (7% ee) was obtained for that of (E)-1-phenyl-1-propene. In the epoxidation of (Z)-olefins, enantioselectivities were in the range of 68-72% ee by using 3 as a catalyst and 60% ee by using 4.

AB - Chiral (salen)manganese(III) complexes (3 and 4) were prepared and used for the enantioselective epoxidation of unfunctionalized olfefins. The highest enantioselectivity of 48% ee for the catalytic epoxidation of (E)-stilbene was realized by using 3 as a catalyst though much lower enantioselectivity (7% ee) was obtained for that of (E)-1-phenyl-1-propene. In the epoxidation of (Z)-olefins, enantioselectivities were in the range of 68-72% ee by using 3 as a catalyst and 60% ee by using 4.

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Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes

Abstract

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