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
1999; Elsevier BV; Volume: 10; Issue: 4 Linguagem: Inglês
10.1016/s0957-4166(99)00036-1
ISSN1362-511X
AutoresHan‐Xun Wei, Jason D. Hook, Keith A. Fitzgerald, Guigen Li,
Tópico(s)Synthesis of β-Lactam Compounds
ResumoA series of new Baylis–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.
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