New chiral oxazoline-phosphite ligands for the enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones

Authors
Escher, IH Pfaltz, A
Citation
Ih. Escher et A. Pfaltz, New chiral oxazoline-phosphite ligands for the enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones, TETRAHEDRON, 56(18), 2000, pp. 2879-2888
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
18
Year of publication
2000
Pages
2879 - 2888
Database
ISI
SICI code
0040-4020(20000428)56:18<2879:NCOLFT>2.0.ZU;2-X
Abstract
A series of new P,N-ligands with a binaphthyl and an oxazoline moiety were prepared, which are efficient ligands for the enantioselective copper-catal yzed 1,4-addition of organozinc reagents to enones. Increasing the steric b ulk in the 3,3'-position of binaphthyl from an H to a biphenylyl moiety imp roved the ee from 65 to 94% in the reaction of diethylzinc with cyclopenten one. (C) 2000 Elsevier Science Ltd. All rights reserved.