A Versatile Method for Kinetic Resolution of Protecting‐Group‐Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation

A challenging direct asymmetric catalytic aerobic oxidative cross‐coupling of 2‐naphthylamine and 2‐naphthol, using a novel CuI/SPDO system, has been successfully developed for the first time. Enantioenriched 3,3′‐disubstituted NOBINs were achieved and could be readily derived to divergent chiral ligands and catalysts. This reaction features high enantioselectivities (up to 96 % ee) and good yields (up to 80 %). The DFT calculations suggest that the F–H interactions between CF3 of L17 and H‐1,8 of 2‐naphthol, and the π–π stacking between the two coupling partners could play vital roles in the enantiocontrol of this cross‐coupling reaction.

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Enantioselective Synthesis of 3,3′‐Disubstituted 2‐Amino‐2′‐hydroxy‐1,1′‐binaphthyls by Copper‐Catalyzed Aerobic Oxidative Cross‐Coupling

Zhao

Ding

et al. 2021

Angewandte Chemie

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Asymmetric Synthesis of Hydroquinolines with α,α‐Disubstitution through Organocatalyzed Kinetic Resolution

et al. 2021

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The first kinetic resolution of hydroquinoline derivatives with a,a-disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate-and enantio-determining electrophilic attack promoted by a network of attractive non-covalent interactions between the substrate and catalyst. Facile subsequent removal and transformations of the newly introduced hydrazine moiety enable these protocols to serve as powerful tools for asymmetric synthesis of N-heterocycles with a,a-disubstitution. Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under:

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Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution

et al. 2021

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The first highly enantioselective Cu I-catalyzed azide-alkyne cycloaddition (CuAAC) of tertiary alcohols and their kinetic resolution is reported. This approach allows facile access to multifunctional tertiary alcohols featuring an a-ethynyl or a-triazole moiety, and represents the first successful kinetic resolution of racemates with a tetrasubstituted carbon stereocenter via CuAAC. Newly developed pyridinebisoxazoline (PYBOX) ligands with a C4 phosphonate group play a key role.

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A Versatile Method for Kinetic Resolution of Protecting‐Group‐Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation

Cited by 17 publications

References 106 publications

Enantioselective Synthesis of 3,3′‐Disubstituted 2‐Amino‐2′‐hydroxy‐1,1′‐binaphthyls by Copper‐Catalyzed Aerobic Oxidative Cross‐Coupling

Enantioselective Synthesis of 3,3′‐Disubstituted 2‐Amino‐2′‐hydroxy‐1,1′‐binaphthyls by Copper‐Catalyzed Aerobic Oxidative Cross‐Coupling

Asymmetric Synthesis of Hydroquinolines with α,α‐Disubstitution through Organocatalyzed Kinetic Resolution

Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution

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