PD(0) CATALYZED ASYMMETRIC AMINATION OF A PROCHIRAL BICYCLIC ALLYLIC DIACETATE

Authors
MUCHOW G BRUNEL JM MAFFEI M PARDIGON O BUONO G
Citation
G. Muchow et al., PD(0) CATALYZED ASYMMETRIC AMINATION OF A PROCHIRAL BICYCLIC ALLYLIC DIACETATE, Tetrahedron, 54(35), 1998, pp. 10435-10448
Citations number
62
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
35
Year of publication
1998
Pages
10435 - 10448
Database
ISI
SICI code
0040-4020(1998)54:35<10435:PCAAOA>2.0.ZU;2-H
Abstract
,3-bis(acetoxymethyl)bicyclo[2.2.1]hepta-2,5-diene 1 undergoes nucleop hilic attack of secondary amines under catalyzed Pd(0) reaction condit ions. The influence of various tertiary amines as acceptor bases on th e reaction as well as the nature of the organophosphorus ligands on th e metal has been investigated. The use of chiral heterocyclic ligands led to the formation of the monoaminated product 2e with enantiomeric excess up to 89%. (C) 1998 Elsevier Science Ltd. All rights reserved.