Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis
نویسندگان
چکیده
منابع مشابه
Organocatalytic regioselective Michael additions of cyclic enones via asymmetric phase transfer catalysis.
Cyclohexanone and cycloheptanone can be enantioselectively functionalized in the 3-position with up to 92% ee and 87% ee, respectively, by the base-promoted dimerization of the corresponding enones using 3,4,5-tribenzyloxybenzyl cinchoninium bromide, as a new effective catalyst.
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The first organocatalytic enantioselective direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactam to nitroolefins is developed using cinchona alkaloids as the catalysts. Both product enantiomers are accessible with moderate to good enantioselectivity.
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A series of chiral pyrrolidinyl-sulfamide derivatives have been identified as efficient bifunctional organocatalysts for the direct Michael addition of cyclohexanone to a wide range of nitroalkenes. The desired Michael adducts were obtained in high chemical yields and excellent stereoselectivities (up to 99/1 dr and 95% ee).
متن کاملAsymmetric Michael addition of aldehydes to nitroalkenes using a primary amino acid lithium salt.
Enantioselective Michael addition of aldehydes to nitroalkenes was successfully carried out by asymmetric catalysis with L-phenylalanine lithium salt, giving gamma-nitroaldehydes in good yields with high enantioselectivity.
متن کاملCatalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins.
A direct vinylogous Michael reaction of γ-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocenters in excellent yield with perfect diastereoselectivity (>20:1 dr) and high enantioselectivity (u...
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ژورنال
عنوان ژورنال: Proceedings of the National Academy of Sciences
سال: 2010
ISSN: 0027-8424,1091-6490
DOI: 10.1073/pnas.1001150107