Diastereoselective synthesis of 1,4-amino alcohols via 1,4-stereochemical control using sulfoximines

Authors
Pyne, SG Dong, ZM
Citation
Sg. Pyne et Zm. Dong, Diastereoselective synthesis of 1,4-amino alcohols via 1,4-stereochemical control using sulfoximines, TETRAHEDR L, 40(33), 1999, pp. 6131-6134
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
33
Year of publication
1999
Pages
6131 - 6134
Database
ISI
SICI code
0040-4039(19990813)40:33<6131:DSO1AV>2.0.ZU;2-L
Abstract
A diastereoselective synthesis of 1,4-amino alcohols can be achieved from a highly diastereoselective reduction of a gamma-keto-vinyl sulfoximine foll owed by C-methylation and then a highly diastereoselective palladium(0) cat alysed allylic sulfoximine to allylic sulfinamide rearrangement with 1,4-st ereochemical control from a remote hydroxyl group. (C) 1999 Published by El sevier Science Ltd. All rights reserved.