Synthesis of a Heteroannulated Furanose via Intramolecular Michael Addition in an ω-Hydroxy α,β-Unsaturated Nitrile
نویسندگان
چکیده
منابع مشابه
Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates.
We report an asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates in the presence of Cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks.
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A convenient synthesis of benzyl-gamma-butyrolactone derivatives via intramolecular Michael addition reaction of nitro-substituted aryl allyl beta-ketocarboxylates is reported. The method features simple operation, mild reaction conditions and high efficiency.
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A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er). These reactions were enabled by a quinine-derived primary-tertiary diamine as a catalyst and pentafluoropropionic acid (PFP) as a co-catalyst.
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An efficient cyclization of 2’-hydroxychalcone to flavanone using calcium chloride as a catalyst was developed. The scope of the reaction was studied with substituted 2’-hydroxychalcone and these chalcones was converted into corresponding flavanone in good yield. The merits of this method are inexpensive and easily available catalyst, easy workup procedure, avoid use of toxic solvent
متن کاملCalcium Chloride catalyzed Intramolecular Oxa Michael addition of 2’-Hydroxychalcone to Flavanone
An efficient cyclization of 2’-hydroxychalcone to flavanone using calcium chloride as a catalyst was developed. The scope of the reaction was studied with substituted 2’-hydroxychalcone and these chalcones was converted into corresponding flavanone in good yield. The merits of this method are inexpensive and easily available catalyst, easy workup procedure, avoid use of toxic solvent.
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ژورنال
عنوان ژورنال: Journal of Chemical Research
سال: 1999
ISSN: 1747-5198,2047-6507
DOI: 10.1177/174751989902300913