Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones

Authors
Bennett, SMW Brown, SM Cunningham, A Dennis, MR Muxworthy, JP Oakley, MA Woodward, S
Citation
Smw. Bennett et al., Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones, TETRAHEDRON, 56(18), 2000, pp. 2847-2855
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
18
Year of publication
2000
Pages
2847 - 2855
Database
ISI
SICI code
0040-4020(20000428)56:18<2847:CACAOO>2.0.ZU;2-1
Abstract
Methods for enantioselective 1,4-addition of main-group organometallics to linear enones are overviewed. Thiourethane and thioether 1,1'-binaphthyl-ba sed ligands are effective for copper-catalysed 1,4-addition of ZnEt2 and Al R3 (R=Me, Et) to trans-alkyl-3-en-2-ones; enantioselectivities of up to 72% e.e. are attained. In comparison 1,4-addition of ZnEt2 to 2-cyclohexenone proceeds in up to 77% e.e. with the same ligand family. (C) 2000 Elsevier S cience Ltd. Ail rights reserved.