Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 19, Pages 8888-8899Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01596
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Funding
- National Natural Science Foundation of China [21632008, 21472209, 21672232, 91229204]
- Major Project of Chinese National Programs for Fundamental Research and Development [2015CB910304]
- National Basic Research Program of China [2012CB518005]
- National S&T Major Projects [2013ZX09507-001, 2014ZX09507002-001]
- China Pharmaceutical University [SKLNMZZCX201404]
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The ubiquitous structure of all-carbospirocyclic oxindoles makes the development of new methods for their enantioselective and stereoselective synthesis a significant ongoing challenge. Herein, we disclose a formal [4 + 2] annulation through N-heterocyclic carbene (NHC) catalysis for highly enantioselective synthesis of intriguing spirocarbocyclic oxindoles in the presence of Lewis acids. This protocol features good substrates tolerance, good yields, and excellent diastereoselectivities and enantioselectivities (up to 97% ee) under mild conditions.
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