Journal ArticleDOI
Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.
Daisuke Uraguchi,Masahiro Terada +1 more
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It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines and functions as an excellent catalyst.Abstract:
It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines. The beneficial effects of the 3,3‘-bisaryl substituents of the catalysts on the enantioselectivity are greatly appreciated, and thus 1d functions as an excellent catalyst. The Bronsted acid-catalyzed direct Mannich reactions presented herein provide an attractive way to construct β-aminoketones under extremely mild conditions. The stereochemical course of this reaction was established through the synthesis of Boc-(S)-phenylglycine methylester. The transformation thus demonstrated is applicable to a useful method for the synthesis of various phenylglycine derivatives.read more
Citations
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Small-molecule H-bond donors in asymmetric catalysis.
Journal ArticleDOI
Asymmetric catalysis by chiral hydrogen-bond donors.
Mark S. Taylor,Eric N. Jacobsen +1 more
TL;DR: This review documents the structural and mechanistic features that contribute to high enantioselectivity in hydrogen-bond-mediated catalytic processes in small-molecule, synthetic catalyst systems.
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.
References
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Journal ArticleDOI
Proline-Catalyzed Direct Asymmetric Aldol Reactions
TL;DR: The finding that the amino acid proline is an effective asymmetric catalyst for the direct aldol reaction between unmodified acetone and a variety of aldehydes is reported.
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New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels−Alder Reaction
TL;DR: In this article, the first highly enantioselective organocatalytic Diels-Alder reaction was reported, which is the state-of-the-art for asymmetric catalysts.
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Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid
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Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts
TL;DR: Michael reaction of malonates to nitrooleolefins with chiral bifunctional organocatalysts, bearing both a thiourea and tertiary amino group, afforded Michael adducts with high yields and enantioselectivities.
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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.