Mechanism of asymmetric sulfimidation with N-alkoxycarbonyl azide in the presence of (OC)Ru(salen) complex

Tatsuya Uchida; Yuusuke Tamura; Masaaki Ohba; Tsutomu Katsuki

doi:10.1016/j.tetlet.2003.08.108

Mechanism of asymmetric sulfimidation with N-alkoxycarbonyl azide in the presence of (OC)Ru(salen) complex

Tatsuya Uchida, Yuusuke Tamura, Masaaki Ohba, Tsutomu Katsuki

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48 Citations (Scopus)

Abstract

Spectroscopic analysis of imidation of alkyl aryl sulfides with N-2,2,2-trichloro-1,1-dimethylethyloxycarbonyl azide 2 in the presence of (OC)Ru(salen) complex 1 strongly suggests that an addition compound of the azide 2 to 1 is the active species for the imidation, while the addition compound undergoes the undesired intramolecular C-H insertion onto the salen ligand of the complex in the absence of sulfide, directly or via the corresponding nitrene-ruthenium species.

Original language	English
Pages (from-to)	7965-7968
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2003.08.108
Publication status	Published - Oct 20 2003

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2003.08.108

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abstract = "Spectroscopic analysis of imidation of alkyl aryl sulfides with N-2,2,2-trichloro-1,1-dimethylethyloxycarbonyl azide 2 in the presence of (OC)Ru(salen) complex 1 strongly suggests that an addition compound of the azide 2 to 1 is the active species for the imidation, while the addition compound undergoes the undesired intramolecular C-H insertion onto the salen ligand of the complex in the absence of sulfide, directly or via the corresponding nitrene-ruthenium species.",

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AU - Uchida, Tatsuya

AU - Tamura, Yuusuke

AU - Ohba, Masaaki

AU - Katsuki, Tsutomu

PY - 2003/10/20

Y1 - 2003/10/20

N2 - Spectroscopic analysis of imidation of alkyl aryl sulfides with N-2,2,2-trichloro-1,1-dimethylethyloxycarbonyl azide 2 in the presence of (OC)Ru(salen) complex 1 strongly suggests that an addition compound of the azide 2 to 1 is the active species for the imidation, while the addition compound undergoes the undesired intramolecular C-H insertion onto the salen ligand of the complex in the absence of sulfide, directly or via the corresponding nitrene-ruthenium species.

AB - Spectroscopic analysis of imidation of alkyl aryl sulfides with N-2,2,2-trichloro-1,1-dimethylethyloxycarbonyl azide 2 in the presence of (OC)Ru(salen) complex 1 strongly suggests that an addition compound of the azide 2 to 1 is the active species for the imidation, while the addition compound undergoes the undesired intramolecular C-H insertion onto the salen ligand of the complex in the absence of sulfide, directly or via the corresponding nitrene-ruthenium species.

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JF - Tetrahedron Letters

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ER -

Mechanism of asymmetric sulfimidation with N-alkoxycarbonyl azide in the presence of (OC)Ru(salen) complex

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