A concise synthesis of homochiral sedamines and related alkaloids. A new reductive application of Jacobsen's catalyst

Authors
Yu, CY Meth-Cohn, O
Citation
Cy. Yu et O. Meth-cohn, A concise synthesis of homochiral sedamines and related alkaloids. A new reductive application of Jacobsen's catalyst, TETRAHEDR L, 40(36), 1999, pp. 6665-6668
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
36
Year of publication
1999
Pages
6665 - 6668
Database
ISI
SICI code
0040-4039(19990903)40:36<6665:ACSOHS>2.0.ZU;2-9
Abstract
Two methods for the generation of both enantiomers of sedamine [1-methyl-2- (2-phenyl-2-hydroxy-1-ethyl)piperidine] in high optical purity have been el aborated The first utilises the lipase-mediated kinetic resolution of racem ic acetates and the second involves the NaBH4 mediated: reduction of ketone s catalysed by Jacobsen's catalyst. Some related applications of these reac tions are also disclosed. (C) 1999 Elsevier Science Ltd. All rights reserve d.