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, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, China
J. Am. Chem. Soc., 2007, 129 (7), pp 1878–1879
DOI: 10.1021/ja068703p
Publication Date (Web): January 31, 2007
Copyright © 2007 American Chemical Society
†

 West China School of Pharmacy, Sichuan University.

,
‡

 Chengdu Institute of Biology.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
§

 West China Hospital, Sichuan University.

, ycchenhuaxi@yahoo.com.cn

Abstract

Abstract Image

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.

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History

  • Published In Issue February 21, 2007
  • Received December 12, 2006

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