Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement

Masakazu Murakami, Tatsuya Uchida, Bunnai Saito, Tsutomu Katsuki

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

(OC)Ru(salen) 1 was found to catalyze sulfimidation of alkyl aryl sulfides in the presence of arylsulfonyl azide with high enantioselectivity, up to 99% ee. When the substrates were allylic sulfides, the resulting sulfimides underwent [2,3]sigmatropic rearrangement to give the corresponding N-allyl toluenesulsulfonamides with greater than 80% ee.

Original languageEnglish
Pages (from-to)116-123
Number of pages8
JournalChirality
Volume15
Issue number2
DOIs
Publication statusPublished - Feb 10 2003

Fingerprint

Sulfides
Azides
Enantioselectivity
Substrates
disalicylaldehyde ethylenediamine

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement. / Murakami, Masakazu; Uchida, Tatsuya; Saito, Bunnai; Katsuki, Tsutomu.

In: Chirality, Vol. 15, No. 2, 10.02.2003, p. 116-123.

Research output: Contribution to journalArticle

Murakami, Masakazu ; Uchida, Tatsuya ; Saito, Bunnai ; Katsuki, Tsutomu. / Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement. In: Chirality. 2003 ; Vol. 15, No. 2. pp. 116-123.
@article{e1738feaa445417a9bb429d86f72f4b3,
title = "Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement",
abstract = "(OC)Ru(salen) 1 was found to catalyze sulfimidation of alkyl aryl sulfides in the presence of arylsulfonyl azide with high enantioselectivity, up to 99{\%} ee. When the substrates were allylic sulfides, the resulting sulfimides underwent [2,3]sigmatropic rearrangement to give the corresponding N-allyl toluenesulsulfonamides with greater than 80{\%} ee.",
author = "Masakazu Murakami and Tatsuya Uchida and Bunnai Saito and Tsutomu Katsuki",
year = "2003",
month = "2",
day = "10",
doi = "10.1002/chir.10156",
language = "English",
volume = "15",
pages = "116--123",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "2",

}

TY - JOUR

T1 - Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement

AU - Murakami, Masakazu

AU - Uchida, Tatsuya

AU - Saito, Bunnai

AU - Katsuki, Tsutomu

PY - 2003/2/10

Y1 - 2003/2/10

N2 - (OC)Ru(salen) 1 was found to catalyze sulfimidation of alkyl aryl sulfides in the presence of arylsulfonyl azide with high enantioselectivity, up to 99% ee. When the substrates were allylic sulfides, the resulting sulfimides underwent [2,3]sigmatropic rearrangement to give the corresponding N-allyl toluenesulsulfonamides with greater than 80% ee.

AB - (OC)Ru(salen) 1 was found to catalyze sulfimidation of alkyl aryl sulfides in the presence of arylsulfonyl azide with high enantioselectivity, up to 99% ee. When the substrates were allylic sulfides, the resulting sulfimides underwent [2,3]sigmatropic rearrangement to give the corresponding N-allyl toluenesulsulfonamides with greater than 80% ee.

UR - http://www.scopus.com/inward/record.url?scp=0037258155&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037258155&partnerID=8YFLogxK

U2 - 10.1002/chir.10156

DO - 10.1002/chir.10156

M3 - Article

C2 - 12520501

AN - SCOPUS:0037258155

VL - 15

SP - 116

EP - 123

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 2

ER -