Pd-Catalyzed Atroposelective C–H Allylation and Alkenylation: Access to Enantioenriched Atropisomers Featuring Pentatomic Heteroaromatics
Sign Up to like & getrecommendations! Published in 2019 at "Organometallics"
DOI: 10.1021/acs.organomet.9b00490
Abstract: The development of efficient and unified synthetic methods to access enantioenriched pentatomic biaryls is extremely challenging, due to the relatively low rotational barriers of these five-membere... read more here.
Keywords: access; alkenylation access; access enantioenriched; atroposelective allylation ... See more keywords
Carbene-Catalyzed Atroposelective Annulation and Desymmetrization of Urazoles.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c01191
Abstract: An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich… read more here.
Keywords: annulation desymmetrization; carbene catalyzed; atroposelective annulation; catalyzed atroposelective ... See more keywords
Rhodium(III)-Catalyzed Atroposelective Synthesis of C-N Axially Chiral Naphthylamines and Variants via C-H Activation.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00686
Abstract: Reported herein is the efficient and atroposelective construction of two categories of C-N atropisomers via rhodium(III)-catalyzed C-H activation of sulfoxonium ylides en route to [4+2] annulation with sterically hindered, electron-rich alkynes. This reaction proceeds with… read more here.
Keywords: axially chiral; catalyzed atroposelective; iii catalyzed; activation ... See more keywords
Rhodium-Catalyzed Atroposelective C-H Arylation of (Hetero)Arenes Using Carbene Precursors as Arylating Reagents.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00968
Abstract: Rhodium(III)-catalyzed C-H activation-based arylation of sterically hindered (hetero)arenes has been realized using diazo compounds and triazoles as arylating reagents for atroposelective synthesis of two classes of biaryls. The coupling of 3-substituted indoles and N-sulfonyltriazoles afforded… read more here.
Keywords: hetero arenes; rhodium catalyzed; arylating reagents; catalyzed atroposelective ... See more keywords
Pd-Catalyzed Atroposelective C-H Acyloxylation Enabling Access to an Axially Chiral Biaryl Phenol Organocatalyst.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01981
Abstract: Herein, we present the Pd(II)-catalyzed atroposelective C-H acyloxylation strategy for the assembly of biaryl aldehyde atropoisomers using readily available amino acids as the catalytic auxiliary and chiral pool. This strategy exhibits a broad substrate scope… read more here.
Keywords: catalyzed atroposelective; phenol organocatalyst; atroposelective acyloxylation;
Phosphine-Catalyzed Atroposelective Formal [3 + 2] Cycloaddition Desymmetrization of N-Arylmaleimides.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02208
Abstract: Herein, a new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was devised by [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This desymmetrization process allows for quick… read more here.
Keywords: phosphine catalyzed; cycloaddition desymmetrization; atroposelective formal; formal cycloaddition ... See more keywords
Palladium/Amino Acid Co-catalyzed Atroposelective C-H Olefination to Access Tetra-Ortho-Substituted Atropisomers Featuring 2,2'-Difluoro-1-biaryl Scaffolds.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02303
Abstract: Despite the great advancement in atroposelective synthesis in the past decades, the enantioselective synthesis of 2,2'-difluoro-1-biaryls is unprecedented. Herein, a palladium and chiral amino acid catalyzed atroposelective C-H olefination to construct the axially chiral 2,2'-difluoro-1-biaryls… read more here.
Keywords: difluoro; atroposelective olefination; amino acid; catalyzed atroposelective ... See more keywords
Palladium-Catalyzed Atroposelective Coupling-Cyclization of 2-Isocyanobenzamides to Construct Axially Chiral 2-Aryl- and 2,3-Diarylquinazolinones.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c00640
Abstract: A palladium-catalyzed imidoylative cycloamidation of N-alkyl-2-isocyanobenzamides with 2,6-disubstituted aryl iodides, affording unprecedented axially chiral 2-arylquinazolinones, has been developed with good yields and atroposelectivities. In this coupling-cyclization process, the biaryl linkage and the heteroaromatic ring are… read more here.
Keywords: palladium catalyzed; coupling cyclization; axially chiral; catalyzed atroposelective ... See more keywords
Ir-Catalyzed Atroposelective Desymmetrization of Heterobiaryls: Hydroarylation of Vinyl Ethers and Bicycloalkenes.
Sign Up to like & getrecommendations! Published in 2020 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.9b12858
Abstract: A highly regio, diastereo- and enantioselective, scalable Ir-catalyzed hydroarylation of electron rich acyclic and tensioned cyclic olefins with heterobiaryls is described. The reaction of acyclic vinyl ethers, dihydrofuran and norbornenes with a variety of aryl… read more here.
Keywords: hydroarylation; atroposelective desymmetrization; vinyl ethers; desymmetrization heterobiaryls ... See more keywords
Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality
Sign Up to like & getrecommendations! Published in 2022 at "Chemical Science"
DOI: 10.1039/d2sc00748g
Abstract: Thioethers allowed for highly atroposelective C–H olefinations by a palladium/chiral phosphoric acid catalytic system under ambient air. Both N–C and C–C axial chiral (hetero)biaryls were successfully constructed, leading to a broad range of axially chiral… read more here.
Keywords: palladium catalyzed; enabled palladium; atroposelective olefination; thioether enabled ... See more keywords
Carbene-Catalyzed Atroposelective Annulation for Quick Access to Axially Chiral Thiazine Derivatives
Sign Up to like & getrecommendations! Published in 2023 at "Molecules"
DOI: 10.3390/molecules28104052
Abstract: An N-heterocyclic carbene (NHC)-catalyzed atroposelective annulation reaction is disclosed for quick and efficient access to thiazine derivatives. A series of axially chiral thiazine derivatives bearing various substituents and substitution patterns were produced in moderate to… read more here.
Keywords: atroposelective annulation; thiazine derivatives; chiral thiazine; thiazine ... See more keywords