Squaramide-Catalyzed Synthesis of Enantioenriched Spirocyclic Oxindoles via Ketimine Intermediates with Multiple Active Sites

Angewandte Chemie
Qiang-Sheng SunGuo-Qiang Lin

Abstract

A new method for the construction of five-membered spirocyclic oxindoles is based on a Michael-Mannich cascade reaction of a ketimine intermediated catalyzed by a bifunctional quinine-derived squaramide. The desired products were obtained in excellent yields (up to 94%) and stereoselectivities (up to >20:1 d.r., >99% ee). A scaled-up variant also proceeded smoothly showing that the one-pot reaction might find application in the synthesis of bioactive-compound libraries.

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Citations

Jan 21, 2017·The Journal of Organic Chemistry·Marta XimenisAntonio Costa
Nov 8, 2016·Organic & Biomolecular Chemistry·Jian-Qiang ZhaoWei-Cheng Yuan
May 18, 2018·Chemical Communications : Chem Comm·Guang-Jian Mei, Feng Shi
Jun 29, 2018·Chemical Society Reviews·Aishun DingRamon Rios
Jun 30, 2019·Organic Letters·Chiara VolpeAlessandra Lattanzi

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