Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides
نویسندگان
چکیده
منابع مشابه
A highly enantioselective, organocatalytic [3+2]-cycloannulation reaction towards the de novo-synthesis of 1-cyclopentenyl-α-keto esters.
We disclose herein a highly enantioselective de novo-synthesis of chiral 1-cyclopentenyl-α-keto esters starting from a simple bis-silyl-1,3-dienediolate and α,β-unsaturated aldehydes via a domino vinylogous Michael-intramolecular Knoevenagel-type condensation. The cyclopentenes proved to be highly versatile and were readily converted into various structural motifs.
متن کاملA convenient enantioselective decarboxylative aldol reaction to access chiral α-hydroxy esters using β-keto acids
We show a convenient decarboxylative aldol process using a scandium catalyst and a PYBOX ligand to generate a series of highly functionalized chiral α-hydroxy esters. The protocol tolerates a broad range of β-keto acids with inactivated aromatic and aliphatic α-keto esters. The possible mechanism is rationalized.
متن کاملA catalytic highly enantioselective direct synthesis of 2-bromo-2-nitroalkan-1-ols through a Henry reaction.
Highly enantiomerically enriched 2-bromo-2-nitroalkan-1-ols are prepared by direct condensation of aliphatic and aromatic aldehydes with bromonitromethane in the presence of a catalytic amount of copper(ii) acetate and a C(1)-symmetric camphor-derived amino pyridine ligand.
متن کاملCatalytic enantioselective aza-Henry reaction with broad substrate scope.
In situ generated azomethines from readily available precursors react with nitromethane in the presence of 120 mol % of CsOH.H2O and 12 mol % of quinine- and cinchonidine-derived quaternary ammonium chlorides to provide the corresponding aza-Henry adducts in good yields and very high selectivities. It represents the first general enantioselective aza-Henry method for azomethines derived from en...
متن کاملEnantioselective One-Pot Synthesis of α-Amino Esters by a Phosphine-Catalyzed [3+2]-Cycloaddition Reaction
Phosphine-catalyzed [3+2]cycloaddition reactions of electron-deficient allenes and alkynes with a,b-unsaturated carbonyl compounds can give access to important highly functionalized cyclopentenes. The seminal example of such a transformation was first reported by Lu et al. in 1995, and its asymmetric version in 1997 by the group of Zhang. However, it took another ten years before the potential ...
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ژورنال
عنوان ژورنال: RSC Advances
سال: 2018
ISSN: 2046-2069
DOI: 10.1039/c8ra00552d