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Organocatalytic and Highly Stereoselective Direct Vinylogous Mannich Reaction

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posted on 21.02.2007, 00:00 by Tian-Yu Liu, Hai-Lei Cui, Jun Long, Bang-Jing Li, Yong Wu, Li-Sheng Ding, Ying-Chun Chen
The first direct asymmetric vinylogous Mannich (AVM) reaction of α,α-dicyanoolefins and N-Boc aldimines was described promoted by a simple chiral bifunctional thiourea-tertairy amine organocatalyst. The reaction was highly efficient (S/C up to 1000) and regio-, stereoselective (generally >99% de, 96 to >99.5% ee) at room temperature for a broad array of substrates. Enantiomerically pure δ-amino acid could be smoothly prepared from the adduct.