Enantioselective Michael addition of malonic esters to benzalacetophenone by using chiral phase transfer catalysts derived from proline-mandelic acid/tartaric acid
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چکیده
منابع مشابه
Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/alkylation.
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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[reaction: see text] The catalytic enantioselective electrophilic fluorination promoted by quaternary ammonium salt from cinchonine as a phase-transfer catalyst is described. Treatment of beta-keto esters with N-fluorobenzenesulfonimide as the fluorine source under mild reaction conditions afforded the corresponding alpha-fluoro beta-keto esters in exellent yields with good to moderate enantiom...
متن کاملChiral Aminophosphines as Catalysts for Enantioselective Double-Michael Indoline Syntheses
The bisphosphine-catalyzed double-Michael addition of dinucleophiles to electron-deficient acetylenes is an efficient process for the synthesis of many nitrogen-containing heterocycles. Because the resulting heterocycles contain at least one stereogenic center, this double-Michael reaction would be even more useful if an asymmetric variant of the reaction were to be developed. Aminophosphines c...
متن کاملEnantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives.
A family of 9-amino(9-deoxy) epicinchonine derivatives, possessing a range of mono- and bidentate hydrogen bond donor groups at the 9-position, were synthesised and evaluated for asymmetric organocatalytic activity in the dimethyl malonate Michael addition to beta-nitrostyrene; thiourea derivative was identified as the most effective bifunctional organic catalyst and found to induce high enanti...
متن کاملEnantioselective Michael Addition of Water
The enantioselective Michael addition using water as both nucleophile and solvent has to date proved beyond the ability of synthetic chemists. Herein, the direct, enantioselective Michael addition of water in water to prepare important β-hydroxy carbonyl compounds using whole cells of Rhodococcus strains is described. Good yields and excellent enantioselectivities were achieved with this method...
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ژورنال
عنوان ژورنال: Journal of Chemical Sciences
سال: 2019
ISSN: 0974-3626,0973-7103
DOI: 10.1007/s12039-019-1642-5