2018
DOI: 10.1002/cctc.201701698
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Dual Brønsted‐acid Organocatalysis: Cooperative Asymmetric Catalysis with Combined Phosphoric and Carboxylic Acids

Abstract: Scheme1.a) BINOL-monophosphoric acids and their modeo fs ubstrate activation, b) actives ite modificationsf or the generation of highly acidic and/or sterically more congested Brønsted-acid catalysts, c) Brønsted-acid assisted Brønsted-acid catalysis for the modulation of catalyst properties.Scheme2.Classification of different types of Brønsted-acid assistedB rønsted-acidcatalysis in this review.a)single-site substrate binding, b) dual-site substrate binding, c) Brønsted-acid as nucleophile [X = (RO) 2 P(for p… Show more

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Cited by 55 publications
(30 citation statements)
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“…[20] In summary,w ea chieved the first direct catalytic highly enantioselectiveF riedel-Crafts-type alkylation to N-unprotected a-ketiminoester,d irectly affording N-unprotected a-tetrasubstituted amino acid derivatives in high yield and high enantioselectivity. [21] Key to the success of this reaction is the use of novel 3-monosubstituted BINOL phosphoric acids rather than conventional 3,3'-disubstituted ones, and our results suggest the importance of attractive interactions between the reactants and the 3-substituents of the catalyst.T hese results also suggest that installation of substituents at both the 3a nd 3'positions is not alwaysn ecessary to give high stereoselectivity.Because BINOL-derivedp hosphoric acids and their analogs are also used in other contexts such as chiral counter anion catalysis [22] and cooperative catalysis, [23] we believe the present finding will influence research in asymmetric catalysis. Accumulation of such information is awaiting and will be reported in due course.…”
mentioning
confidence: 73%
See 1 more Smart Citation
“…[20] In summary,w ea chieved the first direct catalytic highly enantioselectiveF riedel-Crafts-type alkylation to N-unprotected a-ketiminoester,d irectly affording N-unprotected a-tetrasubstituted amino acid derivatives in high yield and high enantioselectivity. [21] Key to the success of this reaction is the use of novel 3-monosubstituted BINOL phosphoric acids rather than conventional 3,3'-disubstituted ones, and our results suggest the importance of attractive interactions between the reactants and the 3-substituents of the catalyst.T hese results also suggest that installation of substituents at both the 3a nd 3'positions is not alwaysn ecessary to give high stereoselectivity.Because BINOL-derivedp hosphoric acids and their analogs are also used in other contexts such as chiral counter anion catalysis [22] and cooperative catalysis, [23] we believe the present finding will influence research in asymmetric catalysis. Accumulation of such information is awaiting and will be reported in due course.…”
mentioning
confidence: 73%
“…Because BINOL-derivedp hosphoric acids and their analogs are also used in other contexts such as chiral counter anion catalysis [22] and cooperative catalysis, [23] we believe the present finding will influence research in asymmetric catalysis. Accumulation of such information is awaiting and will be reported in due course.…”
mentioning
confidence: 73%
“…Cooperative catalysis using organocatalysts and transition metals has become a new tool to access compounds with excellent enantioselectivities which were otherwise difficult to prepare and therefore has gained signicant interest in the chemical community in the recent years. 84,85 Nishibayashi and co-workers in 2011 described an enantioselective propargylic substitution reaction of propargyl acetates 133 with a-branched aldehydes 134, using both the transition metal catalyst (copper complex) and organocatalyst (secondary amine), Scheme 56. 86 It was envisioned that both the copper complex and organocatalyst will simultaneously activate the propargylic ester 133 and aldehyde 134 to promote the enantioselective propargylic alkylation.…”
Section: Copper Derived Catalystsmentioning
confidence: 99%
“…[14] The mechanical linking of subcomponents can be used to spatially arrange multiple functional groups. [15] Last but not least, rotaxanes can display am echanical chirality [16] even in the absence of any classical element of chirality, which makes them interesting candidates for stereoselective catalysis. [17] The numerous and diverse recent research effortsi nt his arena led to the development of rotaxanes as organocatalysts anda sl igandsi nm etal-catalysed processes.…”
Section: Introductionmentioning
confidence: 99%