Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 10, Pages 4340-4346Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00196
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Funding
- National Natural Science Foundation of China [21421062]
- Key laboratory of Elemento-Organic Chemistry
- Collaborative Innovation Center of Chemical Science and Engineering
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A bifunctional squaramide catalyzed enantioselective formal [3 + 3] annulation reaction with pyrazolin-5-ones and nitroallylic acetates has been developed. Densely substituted tetrahydropyrano[2,3-c]pyrazoles with two adjacent stereogenic centers are obtained in a highly stereo controlled manner. Representative transformation of the annulation product to a biologically important fused dihydroisoquinoline is achieved without any appreciable loss in the diastereo- and enantioselectivity.
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