Premium
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.