Organocatalytic and Highly Stereoselective Direct Vinylogous Mannich Reaction

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,...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2007-02, Vol.129 (7), p.1878-1879
Main Authors: Liu, Tian-Yu, Cui, Hai-Lei, Long, Jun, Li, Bang-Jing, Wu, Yong, Ding, Li-Sheng, Chen, Ying-Chun
Format: Article
Language:English
Subjects:
Amines - chemical synthesis
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Nitriles - chemistry
Stereoisomerism
Thiourea - chemistry
Vinyl Compounds - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja068703p