N-Heterocyclic Carbene-Catalyzed Diastereoselective Vinylogous Michael Addition Reaction of γ-Substituted Deconjugated Butenolides
نویسندگان
چکیده
منابع مشابه
N-heterocyclic carbene-catalyzed aza-Michael addition.
Aza-Michael addition of amines, including aromatic and aliphatic amines, with α, β-unsaturated ketones was realized employing N-Heterocyclic Carbene (NHC) as organocatalyst, yielding β-amino ketones with up to 98% yield.
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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The diastereo- and enantioselective direct vinylogous Michael addition reaction of γ-substituted butenolides to 2-enoylpyridines has been achieved. A range of γ,γ-disubstituted butenolide derivatives, bearing two consecutive tri- and tetrasubstituted stereogenic centers, were readily obtained in good yields with excellent stereoselectivities (up to >99 : 1 dr and >99% ee).
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NHC-catalyzed annulation of enals with 2-enoylpyridines or 2-enoylpyridine N-oxides leading to the diastereoselective synthesis of β-lactone-fused cyclopentanes is reported. The reaction proceeds via the generation of homoenolate equivalent intermediates and tolerates a broad range of functional groups.
متن کاملN-heterocyclic carbene-catalyzed highly enantioselective synthesis of substituted dihydropyranopyrazolones.
Highly optically pure multisubstituted dihydropyrano[2,3-c]pyrazol-6-(1H)-ones were synthesized via the N-heterocyclic carbene-catalyzed enantioselective [4 + 2] annulation of α-chloroaldehydes and pyrazolone-derived oxodienes.
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2015
ISSN: 0022-3263,1520-6904
DOI: 10.1021/acs.joc.5b01845