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Organocatalytic and Highly Stereoselective Direct Vinylogous Mannich Reaction

Tian-Yu Liu, Hai-Lei Cui, Jun Long, Bang-Jing Li, Yong Wu, Li-Sheng Ding and Ying-Chun Chen*

*Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China, Email: ycchenhuaxiyahoo.com.cn

T.-Y. Liu, H.-L. Cui, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, J. Am. Chem. Soc., 2007, 129, 1878-1879.

DOI: 10.1021/ja068703p (free Supporting Information)


Abstract

An asymmetric vinylogous Mannich reaction of α,α-dicyanoolefins and N-Boc aldimines is promoted by a simple chiral bifunctional thiourea-tertiary amine organocatalyst. The reaction was highly efficient, regio-, and stereoselective at room temperature for a broad range of substrates.

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Key Words

Organocatalysis, Mannich Reaction, Homoallylic Amines


ID: J48-Y2007-0520