SYNTHESIS OF 3-HYDROXY AND 3-AMINO 2-SUBSTITUTED N-HETEROCYCLES VIA ENAMINE OXIDATION AND AZIRIDINATION

Authors
SUNOSE M ANDERSON KM ORPEN AG GALLAGHER T MACDONALD SJF
Citation
M. Sunose et al., SYNTHESIS OF 3-HYDROXY AND 3-AMINO 2-SUBSTITUTED N-HETEROCYCLES VIA ENAMINE OXIDATION AND AZIRIDINATION, Tetrahedron letters, 39(48), 1998, pp. 8885-8888
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
48
Year of publication
1998
Pages
8885 - 8888
Database
ISI
SICI code
0040-4039(1998)39:48<8885:SO3A32>2.0.ZU;2-F
Abstract
Reaction of the N-sulfonyl heterocyclic enamines (1a/b) under asymmetr ic epoxidation and dihydroxylation reaction conditions leads to 2,3-di hydroxypyrrolidines and piperidines, (2a) and (2b). Only diols are obs erved under aminohydroxylation conditions, but Mn-mediated aziridinati on of (1a) provides a route to the 3-amino-2-methoxypyrrolidine deriva tives (6) and(7). (C) 1998 Elsevier Science Ltd. All rights reserved.