Asymmetric Synthesis of Octahydroindoles via a Domino Robinson Annulation/5-Endo Intramolecular Aza-Michael Reaction
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چکیده
منابع مشابه
Diastereoselective synthesis of epoxide-fused benzoquinolizidine derivatives using intramolecular domino aza-Michael addition/Darzens reaction.
An efficient and diastereoselective strategy based on an intramolecular domino aza-Michael/Darzens reaction to synthesize epoxide-fused benzoquinolizidines has been described. Three bonds (1 C-C, 1 C-N and 1 C-O), three rings and three chiral centers can be constructed in a single pot under very mild conditions. All the products were isolated in only one diastereomer with 40-80% yields.
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A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, β-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogenic centers in good yields, excellent enantiomeric excesses, and up to high diastereomeric ratios.
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An efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via domino intramolecular aza-Michael addition/alkylation was developed. These reactions were enabled by cinchona alkaloid-derived quaternary ammonium salts as the phase-transfer catalyst. A variety of benzoindolizidines were prepared in good yields (up to 93%) and enantioselectivities...
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A formal enantioselective synthesis of benazepril.HCl (4), an anti- hypertensive drug, is reported. Our synthesis employed an asymmetric aza-Michael addition of L-homophenylalanine ethyl ester (LHPE, 1) to 4-(2-nitrophenyl)-4-oxo- but-2-enoic acid methyl ester (6) as the key step to prepare (2S,3'S)-2-(2-oxo-2,3,4,5- tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester (8), ...
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A bifunctional squaramide catalysed aza-Michael/Michael cascade reaction between nitroalkenes and tosylaminomethyl enones or enoates has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chiral pyrrolidines with a broad substrate scope, giving the desired products in good yields (up to 99%) with good diastereoselectivities (up to 91 : 9 dr) and ...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2016
ISSN: 0022-3263,1520-6904
DOI: 10.1021/acs.joc.6b01568