Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides
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DOI: 10.1007/s11426-018-9393-2
Abstract: A highly diastereoselective and enantioselective Michael addition/desymmetrization reaction of maleimides with prochiral 3- substituted phthalides catalyzed by quinine-derived bifunctional thiourea was realized. A broad range of the 3,3′-disubstituted phthalides bearing vicinal quaternary-tertiary stereogenic centers were… read more here.
Keywords: quinine derived; michael addition; enantioselective michael; substituted phthalides ... See more keywords
Isothiourea-Catalyzed Enantioselective Michael Addition of Malonates to α,β-Unsaturated Aryl Esters
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DOI: 10.1021/acs.orglett.2c01486
Abstract: An enantioselective Michael addition of malonates to α,β-unsaturated para-nitrophenyl esters was achieved using the Lewis basic isothiourea HyperBTM, giving excellent levels of product enantioselectivity (up to >99:1 enantiomeric ratio) in good yields and with complete… read more here.
Keywords: addition malonates; malonates unsaturated; michael addition; enantioselective michael ... See more keywords
Enantioselective Michael Addition/Cyclization/Desymmetrization Sequence of Prochiral Cyclic Hemiacetals and Nitroolefins: Synthesis of Chiral Oxygen-Bridged Bicyclic Compounds.
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DOI: 10.1021/acs.orglett.2c03815
Abstract: The organocatalytic enantioselective Michael addition of functionalized prochiral cyclic hemiacetals and nitroolefins has been developed under cooperative enamine and hydrogen bond catalysis. The obtained chiral hemiacetal intermediates could be used in the subsequent diastereocontrolled cyclization/desymmetrization… read more here.
Keywords: michael addition; prochiral cyclic; enantioselective michael; cyclic hemiacetals ... See more keywords
Organocatalytic Enantioselective Michael-Michael-Michael-Aldol Condensation Reactions: Control of Six Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles.
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DOI: 10.1021/acs.orglett.7b02962
Abstract: An organocatalyzed enantioselective Michael-Michael-Michael-aldol cascade reaction for the construction of cyclopentane fused spirooxindoles was achieved. The domino reaction provided the spirooxindoles with six contiguous stereocenters including a quaternary center in good yields (55-64%) with excellent… read more here.
Keywords: michael michael; michael; michael aldol; enantioselective michael ... See more keywords
Development of Chiral, Bifunctional Thiosquaramides: Enantioselective Michael Additions of Barbituric Acids to Nitroalkenes.
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DOI: 10.1021/jacs.7b01115
Abstract: We report a general method for the synthesis of chiral thiosquaramides, a class of bifunctional catalysts not previously described in the literature. Thiosquaramides are found to be more acidic and significantly more soluble in nonpolar… read more here.
Keywords: thiosquaramides enantioselective; chiral bifunctional; enantioselective michael; bifunctional thiosquaramides ... See more keywords