Cupin Variants as a Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes
نویسندگان
چکیده
منابع مشابه
Camphor-derived C1-symmetric chiral diamine organocatalysts for asymmetric Michael addition of nitroalkanes to enones.
A series of stable C(1)-symmetric chiral diamines (2a–2l) were conveniently synthesized by condensing exo-(-)-bornylamine or (+)-(1S,2S,5R)-menthylamine with various commercially available Cbz-protected amino acids. Among them, 2a can efficiently promote the Michael addition of nitroalkanes to a broad scope of enones with high yields (up to 96%) and excellent enantioselectivities (up to 98%) un...
متن کاملEnantioselective organocatalytic direct Michael addition of nitroalkanes to nitroalkenes promoted by a unique bifunctional DMAP-thiourea.
A new catalyst is designed, synthesized, and evaluated for the asymmetric Michael addition of nitroalkanes to nitroalkenes. The obdurate nature of this reaction has made this a formidable challenge to subdue by asymmetric catalysis. The catalyst design includes a thiourea function to activate the nitroalkene by a double H-bond and a 4-dimethylaminopyridine unit to deprotonate the nitroalkane an...
متن کامل-Fluoro- -nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: Efficient stereoselective Michael addition to chalcones
Highly efficient stereoselective 1,4-addition of racemic -fluoronitro(phenylsulfonyl)methane (FNSM) as a fluoromethyl pronucleophile to , -unsaturated ketones using a wide range of chiral organobifunctional catalysts under moderate conditions in the absence of an additional base has been achieved. A series of catalysts was screened for the enantioselective addition of FNSM to chalcones and the ...
متن کاملHighly enantioselective organocatalytic Michael addition of nitroalkanes to 4-oxo-enoates.
A useful Michael addition reaction using nitroalkanes as the nucleophile and 4-oxo-enoates as the Michael acceptor has been disclosed, and the reaction allows expedient access to functionalized chiral gamma-keto esters in high yields and excellent enantioselectivities (up to 98% ee), with a low catalyst loading.
متن کاملChiral squaramide-catalyzed highly diastereo- and enantioselective direct Michael addition of nitroalkanes to nitroalkenes.
An efficient highly diastereo- and enantioselective direct Michael addition of nitroalkanes to nitroalkenes catalyzed by chiral squaramide catalyst has been developed. This organocatalytic reaction with a low catalyst loading (2 mol%) proceeded well to afford synthetically useful 1,3-dinitro compounds in high yields with high diastereoselectivities (up to 95 : 5 dr) and excellent enantioselecti...
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ژورنال
عنوان ژورنال: Angewandte Chemie International Edition
سال: 2020
ISSN: 1433-7851,1521-3773
DOI: 10.1002/anie.202000129