MUKAIYAMA ALDOL AND MICHAEL REACTIONS CATALYZED BY LANTHANIDE IODIDES

Authors
GIUSEPPONE N VANDEWEGHE P MELLAH M COLLIN J
Citation
N. Giuseppone et al., MUKAIYAMA ALDOL AND MICHAEL REACTIONS CATALYZED BY LANTHANIDE IODIDES, Tetrahedron, 54(43), 1998, pp. 13129-13148
Citations number
76
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
43
Year of publication
1998
Pages
13129 - 13148
Database
ISI
SICI code
0040-4020(1998)54:43<13129:MAAMRC>2.0.ZU;2-A
Abstract
Samarium diiodide is an efficient catalyst precursor which allows the formation of condensation products between various carbonyl compounds and ketene silyl acetals or enoxysilanes. With alpha,beta-unsaturated carbonyl compounds, 1,2- or 1,4-additions are observed according to th e structure of the substrate. alpha,beta-Unsaturated ketones yield to enoxysilanes by selective Michael additions. Aldol poducts are isolate d as silyl ethers. The mechanisms of the reactions are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.