Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 3, Pages 535-540Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501303
Keywords
Asymmetric synthesis; Organocatalysis; Domino reactions; Ketones; Enones
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Funding
- South University of Science and Technology of China (SUSTC)
- National Natural Science Foundation of China (NSFC) [21302089]
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Organocatalytic asymmetric domino reactions of -nitro ketones and enones have been developed for the construction of functionalized cyclohexane skeletons with four stereogenic carbon atoms, including one tetrasubstituted carbon stereocenter. 5-Nitropentan-2-one and 6-nitrohexan-3-one reacted with chalcone to afford six-membered carbocycles with four consecutive stereocenters in yields of 51-91% with 81-93% ee and >20:1 dr. In addition, 4-nitro-1-phenylbutan-1-one reacted with 4-arylbut-3-en-2-ones to afford six-membered carbocycles with two double consecutive stereocenters in yields of 59-92% with 89-94% ee and >20:1 dr. Interestingly, both four consecutive and nonconsecutive stereocenters could be constructed by these substrate-controlled domino reactions.
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