Amino Amide Organocatalysts for Asymmetric Michael Addition of β-Keto Esters with β-Nitroolefins
نویسندگان
چکیده
منابع مشابه
Organocatalytic asymmetric direct vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to nitroolefins.
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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Chiral pyrrolidinyl-oxazole-carboxamides were synthesized and used as efficient new organocatalysts for the asymmetric Michael addition of ketones with nitroalkenes under solvent-free conditions. Gratifyingly, the corresponding Michael adducts were obtained in higher yields (up to 99%) and excellent stereoselectivities (up to >99/1 dr and 99% ee). Transition state models have been proposed to a...
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α-Fluoro-α-nitro esters were used as reaction partners in Michael addition to nitroalkenes, and the products were obtained in excellent chemical yields and with high enantioselectivities. Moreover, α-fluoro-α-amino ester with a quaternary α-carbon was prepared for the first time.
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New bifunctional organocatalysts amine-thioureas bearing multiple hydrogen bonding donors were synthesized and applied in catalytic asymmetric Michael addition of acetylacetone to aryl and alkyl nitroolefins. Multiple hydrogen bonding donors play a significant role in accelerating reactions, improving yields and enantioselectivities.
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Asymmetric addition of arylboroxines to β-alkoxyacrylate esters proceeded in the presence of a rhodium complex coordinated with a chiral diene ligand to give high yields of β-alkoxy-β-arylcarboxylic acid esters with very high enantioselectivity.
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ژورنال
عنوان ژورنال: Bulletin of the Chemical Society of Japan
سال: 2019
ISSN: 0009-2673,1348-0634
DOI: 10.1246/bcsj.20180302