Citation: Ye Jianliang, Huang Peiqiang. Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids[J]. Chinese Journal of Organic Chemistry, ;2018, 38(9): 2215-2230. doi: 10.6023/cjoc201806005 shu

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

Ye Jianliang ,
Huang Peiqiang ^,

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

Corresponding author: Huang Peiqiang, pqhuang@xmu.edu.cn
Received Date: 3 June 2018
Revised Date: 22 August 2018
Available Online: 22 September 2018
Fund Project: the Natural Science Foundation of Fujian Province of China 2017J01021the National Natural Science Foundation of China 21332007Project 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)the Chinese Universities Scientific Fund 20720170092the National Natural Science Foundation of China 21472153the Chinese Universities Scientific Fund 20720180024the National Key R & D Program of China 2017YFA0207302

Figures(35)

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.
- vinylogous Mannich reaction,
- silyloxy pyrrole,
- silyloxy furan,
- imine,
- chiral auxiliary,
- asymmetric catalysis,
- alkaloid,
- asymmetric total synthesis
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