Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (9): 2215-2230.DOI: 10.6023/cjoc201806005 Previous Articles     Next Articles

Special Issue: 合成科学



叶剑良, 黄培强   

  1. 福建省化学生物学重点实验室 能源材料化学协同创新中心 厦门大学化学化工学院化学系 厦门 361005
  • 收稿日期:2018-06-03 修回日期:2018-08-22 发布日期:2018-08-22
  • 通讯作者: 黄培强
  • 基金资助:


Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids

Ye Jianliang, Huang Peiqiang   

  1. Fujian Provincial Key Laboratory of Chemical Biology, Collaborative Innovation Center of Chemistry for Energy Materials(iChEM), Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005
  • Received:2018-06-03 Revised:2018-08-22 Published:2018-08-22
  • Contact: 10.6023/cjoc201806005
  • Supported by:

    Project supported by the National Key R&D Program of China (No. 2017YFA0207302), the National Natural Science Foundation of China (Nos. 21332007, 21472153), the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT) of Ministry of Education, the Chinese Universities Scientific Fund (Nos. 20720170092, 20720180024) and the Natural Science Foundation of Fujian Province of China (No. 2017J01021).

Heterocycles (α,β/β,γ-unsaturated-γ-lactones, α,β-unsaturated-γ-lactams)-based vinylogous Mannich reactions (VMR) constitute a class of effective C-C bond formation approach to install vicinal aminol-containing α,β-unsaturated-lactones and vicinal diamine-containing α,β-unsaturated-γ-lactams. Possessing multiple functionalities, the latters are versatile building blocks for the synthesis of O-heterocycles, N-heterocycles and the synthesis of alkaloids. The progresses of the asymmetric vinylogous Mannich reactions of silyloxy pyrroles and silyloxy furans from 2011 to mid-2018 are summarized. The methods are organized according to chiral auxiliary-induced asymmetric VMRs, asymmetric VMRs catalyzed by metal-chiral ligand complex or organocatalyst, and the applications of the aymmetric VMRs to the syntheses of complex alkaloids. Some limitations of the developed heterocycles-based VMRs are also briefly discussed.

Key words: vinylogous Mannich reaction, silyloxy pyrrole, silyloxy furan, imine, chiral auxiliary, asymmetric catalysis, alkaloid, asymmetric total synthesis