Regioselective Synthesis of Functionalized Dihydroquinolines via Organocatalytic Allylic Alkylation

doi:10.1007/s40242-016-5481-3

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (4): 634-640.doi: 10.1007/s40242-016-5481-3

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Regioselective Synthesis of Functionalized Dihydroquinolines via Organocatalytic Allylic Alkylation

MA Xiaoyuan¹, WU Yi¹, ZHANG Yanjing², TENG Lesheng³, XIE Jing³, LIAO Weiwei²

1. Department of Pharmacology, School of Pharmaceutical Science, Jilin University, Changchun 130021, P. R. China;

2. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012, P. R. China;
3. College of Life Sciences, Jilin University, Changchun 130012, P. R. China

Received:2015-12-12 Revised:2016-01-08 Online:2016-08-01 Published:2016-03-28
Contact: XIE Jing, LIAO Weiwei E-mail:xiejing@jlu.edu.cn;wliao@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21372096).

Abstract

Abstract:

The regioselective allylic alkylation of 1,2-dihydroquinolines and Morita-Baylis-Hillman(MBH) adducts has been developed. By surveying various reaction parameters, we summarized the effects of temperatures, relative reactant doses, catalysts, solvents and N-protected groups on the regioselectivity of this transformation. This method provides a facile protocol for the preparation of allylic α-substituted dihydroquinolines.

Key words: 1,2-Dihydroquinoline, Regioselectivity, Allylic alkylation

MA Xiaoyuan, WU Yi, ZHANG Yanjing, TENG Lesheng, XIE Jing, LIAO Weiwei. Regioselective Synthesis of Functionalized Dihydroquinolines via Organocatalytic Allylic Alkylation[J]. Chemical Research in Chinese Universities, 2016, 32(4): 634-640.

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Regioselective Synthesis of Functionalized Dihydroquinolines via Organocatalytic Allylic Alkylation

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