Treatment of N-Boc derivatives of beta-amino alcohols with N,N-diethylaminosulfur trifluoride leads to chiral oxazolidinones: An unexpected intramolecular cyclization

Authors
Zhao, H Thurkauf, A
Citation
H. Zhao et A. Thurkauf, Treatment of N-Boc derivatives of beta-amino alcohols with N,N-diethylaminosulfur trifluoride leads to chiral oxazolidinones: An unexpected intramolecular cyclization, SYNLETT, (8), 1999, pp. 1280-1282
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
8
Year of publication
1999
Pages
1280 - 1282
Database
ISI
SICI code
0936-5214(199908):8<1280:TONDOB>2.0.ZU;2-J
Abstract
Chiral 2-oxazolidinones were produced in good yields by treatment of N-tert -butoxycarbonyl derivatives of p-amino alcohols with N,N-Diethylaminosulfur Trifluoride (DAST) under mild reaction conditions. An intramolecular nucle ophilic attack mechanism is proposed to explain the formation of the hetero cycles.