Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 20, Pages 4342-4350Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402159
Keywords
Asymmetric synthesis; Organocatalysis; Domino reactions; Oxygen heterocycles; Enantioselectivity
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Funding
- National Natural Science Foundation of China (NSFC) [21202084, 21142009]
- Tianjin Natural Science Foundation of China [12JCQNJC03500 me]
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An asymmetric organocatalytic quadruple cascade reaction was developed for the stable and sterically hindered 2-hydroxychalcones and substituted cinnamaldehydes. This process proceeded through an oxa-Michael-Michael-Michaelaldol condensation to afford highly functionalized tetrahydro-6H-benzo[c] chromene derivatives with high dia-stereoselectivity and enantioselectivity (>99% ee). The structure of adduct 4g with five stereocenters was unambiguously confirmed by single-crystal X-ray diffraction, and valuable mass spectrometry data provided direct support for the proposed reaction mechanism.
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