The asymmetric synthesis of polycyclic 3-spirooxindole alkaloids via the cascade reaction of 2-isocyanoethylindoles.

Chem Commun (Camb)

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, P. R. China.

Published: November 2015


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Article Abstract

A highly enantioselective dearomative cascade reaction between 2-isocyanoethylindoles and 3-alkenyl-oxindoles was realized using a chiral N,N'-dioxide-Mg(II) complex catalyst. This reaction provides a straightforward access to polycyclic 3-spirooxindoles bearing cyclopenta[b]indole units with four contiguous stereocenters in excellent yields and moderate to good stereoselectivities via a Michael/Friedel-Crafts/Mannich cascade.

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http://dx.doi.org/10.1039/c5cc06353aDOI Listing

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