Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 45, Pages 13253-13257Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506206
Keywords
asymmetric synthesis; ketimines; Mannich reactions; Michael additions; nitrogen heterocycles; organocatalysis
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Funding
- National Natural Science Foundation of China [21342009, 21472019]
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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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