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

Murakami Masakazu | Zendy; Uchida Tatsuya | Zendy; Saito Bunnai | Zendy; Katsuki Tsutomu | Zendy

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

Author(s) -

Murakami Masakazu,

Uchida Tatsuya,

Saito Bunnai,

Katsuki Tsutomu

Publication year - 2002

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.10156

Subject(s) - chemistry , sigmatropic reaction , allylic rearrangement , azide , aryl , medicinal chemistry , catalysis , alkyl , enantioselective synthesis , stereochemistry , organic chemistry

(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. Chirality 15:116–123, 2003. © 2003 Wiley‐Liss, Inc.

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