Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2187-2194.DOI: 10.6023/cjoc201406038 Previous Articles     Next Articles


秦天游a,b, 张晓安a,b, 寮渭巍b   

  1. a 大连理工大学精细化工国家重点实验室 大连 116024;
    b 吉林大学化学学院 长春 130012
  • 收稿日期:2014-06-23 修回日期:2014-08-03 发布日期:2014-08-11
  • 通讯作者: 寮渭巍,
  • 基金资助:


Lewis Base-Catalyzed Allylic Alkylation of α-Amino Nitriles and Cyanohydrins and Synthetic Applications

Qin Tianyoua,b, Zhang Sean Xiao-Ana,b, Liao Weiweib   

  1. a State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024;
    b Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012
  • Received:2014-06-23 Revised:2014-08-03 Published:2014-08-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21372096).

This article summarized our recent progress in Lewis base-catalyzed the direct allylic substitutions of Morita-Baylis-Hillman (MBH) adducts with α-amino nitriles and cyanohydrins bearing an α-hydrogen, which provided efficient access to functionalized α-amino nitriles and cyanohydrins incorporating quaternary carbon centers. On the basis of these, a novel metal-free carbocyanation (alkenylcyanation and acylcyanation) approach to construct functionalized nitriles incorporating β-quaternary carbon center has been developed. In addition, the several factors influencing these chemical transformations are discussed, and the possible mechanism is proposed.

Key words: allylic alkylation, Lewis base, catalysis, α-amino nitriles, cyanohydrins, carbocyanation