Oxazepines and thiazepines, 36. Diastereoselective sulfoxidation of 2,3-dyhydro-1,5-benzothiazepin-4(5H)-ones by dimethyldioxirane

Authors
Patonay, T Adam, W Jeko, J Kover, KE Levai, A Nemeth, M Peters, K
Citation
T. Patonay et al., Oxazepines and thiazepines, 36. Diastereoselective sulfoxidation of 2,3-dyhydro-1,5-benzothiazepin-4(5H)-ones by dimethyldioxirane, HETEROCYCLE, 51(1), 1999, pp. 85-94
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
51
Issue
1
Year of publication
1999
Pages
85 - 94
Database
ISI
SICI code
0385-5414(19990101)51:1<85:OAT3DS>2.0.ZU;2-I
Abstract
The highly chemoselective dimethyldioxirane oxidation of 2-substituted 2,3- dihydro-1,5-benzothiazepin-4(5H)-one (1) allows the synthesis of the corres ponding sulfoxides (2) or sulfones (3) in good yields. The relative stereoc hemistry of the sulfoxides has been unequivocally determined by X-Ray and N MR methods. The high trans diastereoselectivity can be explained on the bas is of steric control.