A highly enantioselective benzothiepine synthesis

Authors
Wang, CC Li, JJ Huang, HC Lee, LF Reitz, DB
Citation
Cc. Wang et al., A highly enantioselective benzothiepine synthesis, J ORG CHEM, 65(9), 2000, pp. 2711-2715
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
9
Year of publication
2000
Pages
2711 - 2715
Database
ISI
SICI code
0022-3263(20000505)65:9<2711:AHEBS>2.0.ZU;2-7
Abstract
A highly enantioselective synthesis of benzothiepine la has been accomplish ed via an enantioenriched sulfoxide intermediate obtained by asymmetric oxi dation with a chiral oxaziridine in 89:11 er. The key step is a thermodynam ically controlled asymmetric cyclization reaction that produces two new ste reogenic centers. The (4R,5R) isomer 1a was obtained in 98:2 er.