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

Han Xun Wei, Jason D. Hook, Keith A. Fitzgerald, Guigen Li

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

A series of new Bayils-Hillman adducts, β-monosubstituted and β,β- disubstituted N-(p-toluenesulfinyl)-α-(aminoalkyl)acrylates has been synthesized via asymmetric nucleophilic additions of (α- carbalkoxyvinyl)cuprates to chiral p-toluenesulfinimines. Modest to good yields (52.0-72.0%) and excellent diastereoselectivity (>90% de) have been obtained. The Z/E selectivity was found to be effected by solvents or cosolvents.

Original languageEnglish
Pages (from-to)661-665
Number of pages5
JournalTetrahedron Asymmetry
Volume10
Issue number4
DOIs
StatePublished - Feb 26 1999

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