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 language | English |
|---|---|
| Pages (from-to) | 661-665 |
| Number of pages | 5 |
| Journal | Tetrahedron Asymmetry |
| Volume | 10 |
| Issue number | 4 |
| DOIs | |
| State | Published - Feb 26 1999 |
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Wei, H. X., Hook, J. D., Fitzgerald, K. A., & Li, G. (1999). 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. Tetrahedron Asymmetry, 10(4), 661-665. https://doi.org/10.1016/S0957-4166(99)00036-1