Journal ArticleDOI
Design of chiral N-triflyl phosphoramide as a strong chiral Brønsted acid and its application to asymmetric Diels-Alder reaction.
TLDR
A highly reactive and acidic chiral Brønsted acid catalyst, chiral N-triflyl phosphoramide, was developed and highly enantioselective Diels-Alder reaction of alpha,beta-unsaturated ketone with silyloxydiene was demonstrated.Abstract:
A highly reactive and acidic chiral Bronsted acid catalyst, chiral N-triflyl phosphoramide, was developed. Highly enantioselective Diels-Alder reaction of alpha,beta-unsaturated ketone with silyloxydiene was demonstrated using this chiral Bronsted acid catalyst.read more
Citations
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Journal ArticleDOI
Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates
Journal ArticleDOI
Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon–carbon bond forming reactions
TL;DR: Binaphthol-derived monophosphoric acids have been designed as novel chiral Brønsted-acid catalysts, which function as efficient enantioselective catalysts for a variety of organic transformations, especially for carbon-carbon bond forming reactions.
Journal ArticleDOI
Asymmetric ion-pairing catalysis.
Katrien Brak,Eric N. Jacobsen +1 more
TL;DR: This review describes developments in the burgeoning field of asymmetric ion-pairing catalysis with an emphasis on the insights that have been gleaned into the structural and mechanistic features that contribute to high asymmetric induction.
Journal ArticleDOI
Asymmetric Counteranion-Directed Catalysis: Concept, Definition, and Applications
Manuel Mahlau,Benjamin List +1 more
TL;DR: This Review closes this gap by providing a clear definition of ACDC and by examining both clear cases as well as more ambiguous examples to illustrate the differences and overlaps with other catalysis concepts.
References
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Journal ArticleDOI
Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid
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Metal-free organocatalysis through explicit hydrogen bonding interactions
TL;DR: This field is briefly reviewed here, along with some rough guidelines and concepts for further catalyst development, which offers attractive alternatives to metal (ion)-catalyzed reactions by combining supramolecular recognition with chemical transformations in an environmentally benign fashion.
Journal ArticleDOI
π-Nucleophilicity in Carbon−Carbon Bond-Forming Reactions
TL;DR: In this article, a new method of parametrization was proposed that facilitates a continuous extension of the data sets without the need for reparameterization of existing data, and adjusts the N and s parameters of all presently characterized π-nucleophiles (arenes, alkenes, organometallics).
Journal ArticleDOI
The First General Enantioselective Catalytic Diels−Alder Reaction with Simple α,β-Unsaturated Ketones
TL;DR: The first general approach to enantioselective catalysis of the Diels−Alder reaction with simple ketone dienophiles has been accomplished with the use of iminium catalysis and a new chiral amine catalyst has been developed that allows a variety of monodentate cyclic and acyclic ketones to successfully participate in enantiosedive [4 + 2] cycloadditions.
Journal ArticleDOI
Broad-Spectrum Enantioselective Diels−Alder Catalysis by Chiral, Cationic Oxazaborolidines
TL;DR: The cationic chiral Lewis acids 1 and 2, generated by triflic acid protonation of the corresponding neutral oxazaborolidines, serve as excellent catalysts for Diels-Alder addition of cyclopentadiene to a wide variety of dienophiles.
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Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid
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