DIASTEREOSELECTIVE 5-EXO-TRIG RADICAL CYCLIZATION ON N-ACRYLOYL-TETRAHYDRO-1,3-OXAZINES - A NOVEL-APPROACH TO ENANTIOPURE 3-SUBSTITUTED PYRROLIDINES

Authors
ANDRES C DUQUESOLADANA JP IGLESIAS JM PEDROSA R
Citation
C. Andres et al., DIASTEREOSELECTIVE 5-EXO-TRIG RADICAL CYCLIZATION ON N-ACRYLOYL-TETRAHYDRO-1,3-OXAZINES - A NOVEL-APPROACH TO ENANTIOPURE 3-SUBSTITUTED PYRROLIDINES, Tetrahedron letters, 37(50), 1996, pp. 9085-9086
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
50
Year of publication
1996
Pages
9085 - 9086
Database
ISI
SICI code
0040-4039(1996)37:50<9085:D5RCON>2.0.ZU;2-9
Abstract
loyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbo n-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leadi ng to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromat ographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemic al yield. Copyright (C) 1996 Elsevier Science Ltd