Regio- and stereoselective 6-exo-trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines

Authors
Pedrosa, R Andres, C Duque-Soladana, JP Roson, CD
Citation
R. Pedrosa et al., Regio- and stereoselective 6-exo-trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines, TETRAHEDR-A, 11(13), 2000, pp. 2809-2821
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
13
Year of publication
2000
Pages
2809 - 2821
Database
ISI
SICI code
0957-4166(20000714)11:13<2809:RAS6RC>2.0.ZU;2-U
Abstract
Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselect ive 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8 )-amino menthol. The diastereoselective cyclisation is promoted by tributyl tin hydride, and the competitive 1,5-hydrogen migration depends on the posi tion of the acceptor double bond and the radical site. (C) 2000 Elsevier Sc ience Ltd. All rights reserved.