Regioselective synthesis of functionalized dihydroquinolines via organocatalytic allylic alkylation

Xiaoyuan Ma , Yi Wu , Yanjing Zhang , Lesheng Teng , Jing Xie , Weiwei Liao

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (4) : 634 -640.

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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

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Abstract

The regioselective allylic alkylation of 1,2-dihydroquinolines and Morita-Baylis-Hillman(MBH) adducts has been developed. By surveying various reaction parameters, we summarize 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.

Keywords

1,2-Dihydroquinoline / Regioselectivity / Allylic alkylation

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Xiaoyuan Ma, Yi Wu, Yanjing Zhang, Lesheng Teng, Jing Xie, Weiwei Liao. Regioselective synthesis of functionalized dihydroquinolines via organocatalytic allylic alkylation. Chemical Research in Chinese Universities, 2016, 32(4): 634-640 DOI:10.1007/s40242-016-5481-3

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