Direct Asymmetric Aza-Vinylogous Mannich Reaction of Nitrones from Isatins and Ketimines
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چکیده
منابع مشابه
Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with N-gulosyl nitrones.
Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with L-gulose-derived chiral nitrones in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate was investigated. The selectivity was strongly influenced by the bulkiness of the C-substituent of the nitrone: for example, C-benzyloxymethyl nitrone afforded four stereoisomers, whereas bulky C-[(4S)-2,2...
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An enantio- and diastereoselective direct vinylogous Mannich reaction of alpha,alpha-dicyanoolefins and N-sulfonyl alkylimines has been developed by the catalysis of a new family of bifunctional organocatalysts merging chiral BINOL and 9-amino-9-deoxyepi-cinchona alkaloid skeletons, from which chiral beta-, delta- or gamma-amino compounds could be efficiently derived.
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The diastereospecific formation of β-N-glycoside-linked α-amino-2(5H)-furanone has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and ZnCl(2)·Et(2)O as a promoter in Et(2)O. Imines 3 of aromatic compounds and trimethylsiloxyfuran 4 were converted to N-galactosyl α-amino-2(5H)-furanone 5, ...
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The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized alpha- and beta-am...
متن کاملProtease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent
We reported the first enzyme-catalysed, direct, three-component asymmetric Mannich reaction using protease type XIV from Streptomyces griseus (SGP) in acetonitrile. Yields of up to 92% with enantioselectivities of up to 88% e.e. and diastereoselectivities of up to 92:8 (syn:anti) were achieved under the optimised conditions. This enzyme's catalytic promiscuity expands the application of this bi...
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ژورنال
عنوان ژورنال: Acta Chimica Sinica
سال: 2017
ISSN: 0567-7351
DOI: 10.6023/a17060277