Enantioselective Synthesis of Polysubstituted Tetrahydroquinolines via an Organocatalytic Asymmetric Cascade Reaction

LUO Yongchun; HAN Ronggang; XU Pengfei

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Enantioselective Synthesis of Polysubstituted Tetrahydroquinolines via an Organocatalytic Asymmetric Cascade Reaction

LUO Yongchun #,HAN Ronggang,XU Pengfei *

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000

*Correspondence author

#Submitted by

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Funding: Specialized Research Fund for the Doctoral Program of Higher Education（No.20110211120017）

Opened online: 4 December 2015

Accepted by: none

Citation: LUO Yongchun,HAN Ronggang,XU Pengfei.Enantioselective Synthesis of Polysubstituted Tetrahydroquinolines via an Organocatalytic Asymmetric Cascade Reaction[OL]. [ 4 December 2015] http://en.paper.edu.cn/en_releasepaper/content/4665107

Based on the principles of organocatalysis. An enantioselective and efficient catalytic method for synthesis of polysubstituted tetrahydroquinolines via an aldol/nucleophilic addition cascade reaction was developed. This domino process affords a series of tetrahydroquinoline products with good yields (up to 89%) and high diastereo- and enantiocontrol (dr up to >25:1, ee up to 97%). The structre of the products was characterized by NMR, IR, HR Ms and X-ray differaction. In addition, using some simple reactions, the product structure can be easily modified.

Keywords:Organic Synthesis; Cascade Reaction; Cyclization; Organocatalysis; Tetrahydroquinolines

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