Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 37, Pages 9600-9609Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob01211b
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Funding
- National Natural Science Foundation of China [21272024]
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An efficient protocol for the asymmetric construction of enantiomerically enriched tetrahydro-6H-benzo-[c]chromenes and their derivatives has been developed. The corresponding products were obtained by the cascade double Michael addition of 3-nitro-2H-chromenes and their derivatives with alpha,beta-unsaturated ketones catalyzed by a combination of a quinine-derived primary amine and benzoic acid. Through this methodology, the desired products could be obtained in moderate to good yields (up to 90%), with excellent diastereoselectivities (up to >25 : 1 dr) and moderate to excellent enantioselectivities (up to 95% ee).
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