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

Yuusuke Tamura, Tatsuya Uchida, Tsutomu Katsuki

Research output: Contribution to journalArticle

45 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 languageEnglish
Pages (from-to)3301-3303
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number16
DOIs
Publication statusPublished - Apr 14 2003

Fingerprint

Azides
Enantioselectivity
Sulfides
Reaction rates
Catalysts
Temperature
phenylnitrene
disalicylaldehyde ethylenediamine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Highly enantioselective (OC)Ru(salen)-catalyzed sulfimidation using N-alkoxycarbonyl azide as nitrene precursor. / Tamura, Yuusuke; Uchida, Tatsuya; Katsuki, Tsutomu.

In: Tetrahedron Letters, Vol. 44, No. 16, 14.04.2003, p. 3301-3303.

Research output: Contribution to journalArticle

@article{a385b1b1295d4185a2366e473a1b9121,
title = "Highly enantioselective (OC)Ru(salen)-catalyzed sulfimidation using N-alkoxycarbonyl azide as nitrene precursor",
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.",
author = "Yuusuke Tamura and Tatsuya Uchida and Tsutomu Katsuki",
year = "2003",
month = "4",
day = "14",
doi = "10.1016/S0040-4039(03)00609-9",
language = "English",
volume = "44",
pages = "3301--3303",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "16",

}

TY - JOUR

T1 - Highly enantioselective (OC)Ru(salen)-catalyzed sulfimidation using N-alkoxycarbonyl azide as nitrene precursor

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.

UR - http://www.scopus.com/inward/record.url?scp=0037436984&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037436984&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(03)00609-9

DO - 10.1016/S0040-4039(03)00609-9

M3 - Article

AN - SCOPUS:0037436984

VL - 44

SP - 3301

EP - 3303

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 16

ER -