Highly enantioselective (OC)Ru(salen)-catalyzed sulfimidation using N-alkoxycarbonyl azide as nitrene precursor

Yuusuke Tamura; Tatsuya Uchida; Tsutomu Katsuki

doi:10.1016/S0040-4039(03)00609-9

Highly enantioselective (OC)Ru(salen)-catalyzed sulfimidation using N-alkoxycarbonyl azide as nitrene precursor

Yuusuke Tamura, Tatsuya Uchida, Tsutomu Katsuki

Division for Experimental Natural Science

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

51 Citations (Scopus)

Abstract

Enantioselective imidation of alkyl aryl sulfides with N-alkoxycarbonyl azide as a nitrene precursor was effected by using (OC)Ru(salen) complex 1 as catalyst. The steric and electronic nature of the N-alkoxycarbonyl group was found to strongly affect the enantioselectivity and the reaction rate, and high enantioselectivity (up to 99% ee) and good chemical yields were achieved by using 2,2,2-trichloro-1,1-dimethylethoxycarbonyl azide as the nitrene precursor at room temperature.

Original language	English
Pages (from-to)	3301-3303
Number of pages	3
Journal	Tetrahedron Letters
Volume	44
Issue number	16
DOIs	https://doi.org/10.1016/S0040-4039(03)00609-9
Publication status	Published - Apr 14 2003

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)00609-9

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abstract = "Enantioselective imidation of alkyl aryl sulfides with N-alkoxycarbonyl azide as a nitrene precursor was effected by using (OC)Ru(salen) complex 1 as catalyst. The steric and electronic nature of the N-alkoxycarbonyl group was found to strongly affect the enantioselectivity and the reaction rate, and high enantioselectivity (up to 99% ee) and good chemical yields were achieved by using 2,2,2-trichloro-1,1-dimethylethoxycarbonyl azide as the nitrene precursor at room temperature.",

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AU - Tamura, Yuusuke

AU - Uchida, Tatsuya

AU - Katsuki, Tsutomu

PY - 2003/4/14

Y1 - 2003/4/14

N2 - Enantioselective imidation of alkyl aryl sulfides with N-alkoxycarbonyl azide as a nitrene precursor was effected by using (OC)Ru(salen) complex 1 as catalyst. The steric and electronic nature of the N-alkoxycarbonyl group was found to strongly affect the enantioselectivity and the reaction rate, and high enantioselectivity (up to 99% ee) and good chemical yields were achieved by using 2,2,2-trichloro-1,1-dimethylethoxycarbonyl azide as the nitrene precursor at room temperature.

AB - Enantioselective imidation of alkyl aryl sulfides with N-alkoxycarbonyl azide as a nitrene precursor was effected by using (OC)Ru(salen) complex 1 as catalyst. The steric and electronic nature of the N-alkoxycarbonyl group was found to strongly affect the enantioselectivity and the reaction rate, and high enantioselectivity (up to 99% ee) and good chemical yields were achieved by using 2,2,2-trichloro-1,1-dimethylethoxycarbonyl azide as the nitrene precursor at room temperature.

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SN - 0040-4039

VL - 44

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EP - 3303

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Highly enantioselective (OC)Ru(salen)-catalyzed sulfimidation using N-alkoxycarbonyl azide as nitrene precursor

Abstract

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