Asymmetric synthesis of beta-monosubstituted and beta,beta-disubstituted N-(p-toluenesulfinyl)-alpha-(aminoalkyl)acrylates via anionic additions of (alpha-carbalkoxyvinyl)cuprates to thiooxime S-oxides

Authors
Wei, HX Hook, JD Fitzgerald, KA Li, GG
Citation
Hx. Wei et al., Asymmetric synthesis of beta-monosubstituted and beta,beta-disubstituted N-(p-toluenesulfinyl)-alpha-(aminoalkyl)acrylates via anionic additions of (alpha-carbalkoxyvinyl)cuprates to thiooxime S-oxides, TETRAHEDR-A, 10(4), 1999, pp. 661-665
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
4
Year of publication
1999
Pages
661 - 665
Database
ISI
SICI code
0957-4166(19990226)10:4<661:ASOBAB>2.0.ZU;2-T
Abstract
A series of new Baylis-Hillman adducts, beta-monosubstituted and beta,beta- disubstituted N-(p-toluenesulfinyl)-alpha-(aminoalkyl)acrylates has been sy nthesized via asymmetric nucleophilic additions of (alpha-carbalkoxyvinyl)c uprates to chiral p-toluenesulfinimines. Modest to good yields (52.0-72.0%) and excellent diastereoselectivity (>90% de) have been obtained. The Z/E s electivity was found to be effected by solvents or cosolvents. (C) 1999 Els evier Science Ltd. All rights reserved.