Enamine Carboxylates as Stereodetermining Intermediates in Prolinate Catalysis
نویسندگان
چکیده
منابع مشابه
Enamine carboxylates as stereodetermining intermediates in prolinate catalysis.
Experimental and computational studies probing the nature of intermediates in the α-amination of aldehydes catalyzed by prolinate salts support an enamine carboxylate intermediate in the stereodetermining step.
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An enamine intermediate is believed to be the central feature of biological catalysts, such as aldolases and small molecule amine organocatalysts. Despite decades of investigation of naturally occurring aldolase enzymes and recent studies on designed aldolase antibodies and organocatalysts, direct structural observation of an enamine intermediate has proven to be rare. Herein, we report the obs...
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An octahedral bis-cyclometalated iridium(III) complex catalyzes the enantioselective α-amination of aldehydes with catalyst loadings down to 0.1 mol%. In this metal-templated design, the metal serves as a structural center and provides the exclusive source of chirality, whereas the catalysis is mediated through the organic ligand sphere.
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Recently, we reported the spectroscopic and kinetic characterizations of cytochrome P450 compound I in CYP119A1, effectively closing the catalytic cycle of cytochrome P450-mediated hydroxylations. In this minireview, we focus on the developments that made this breakthrough possible. We examine the importance of enzyme purification in the quest for reactive intermediates and report the preparati...
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We describe herein an unprecedented asymmetric α-amination of β-ketocarbonyls under aerobic conditions. The process is enabled by a simple chiral primary amine through the coupling of a catalytic enamine ester intermediate and a nitrosocarbonyl (generated in situ) derived from N-hydroxycarbamate. The reaction features high chemoselectivity and excellent enantioselectivity for a broad range of s...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2011
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol2023533