Asymmetric Dearomative Fluorination of 2‐Naphthols with a Dicarboxylate Phase‐Transfer Catalyst

Egami, Hiromichi; Rouno, Taiki; Niwa, Tomoki; Masuda, Kousuke; Yamashita, Kenji; Hamashima, Yoshitaka

doi:10.1002/ange.202005367

Cited by 8 publications

(1 citation statement)

References 76 publications

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“…The authors proposed that the source of enantiodiscrimination is hydrogen‐bonding interaction between dicarboxylic acid phase‐transfer catalyst ( S , S )‐ CAT29 and the phenolic hydroxy group of the substrate. The presence of a 3‐substituent greatly decreased the enantioselectivity [125] …”

Section: Asymmetric C−f Bond‐forming Reactions Using Chiral Phase‐transfer Catalysismentioning

confidence: 99%

Asymmetric Methods for Carbon‐Fluorine Bond Formation

et al. 2021

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In memory of Ferenc FülöpAs a consequence of the ever-increasing relevance of fluorinated drugs in medicinal chemistry, organofluorine chemistry has become a hot topic research area during the last decade. Asymmetric carbon-fluorine bond-forming reactions have enormously developed in recent years with considerable findings related to novel reactions and synthetic approaches. These new synthetic efforts have contributed to the access to a growing number of fluorinated molecules and complex natural or synthetic products of high relevance in medicinal chemistry and drug research. Illustrative examples of novel synthetic methodologies, including organocatalytic processes, asymmetric syntheses or phase-transfer catalytic methods for the enantioselective incorporation of fluorine atom(s) into versatile molecular entities, are covered in the current Review, focusing on main contributions of the last ten years.

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Section: Asymmetric C−f Bond‐forming Reactions Using Chiral Phase‐transfer Catalysismentioning

confidence: 99%

Asymmetric Methods for Carbon‐Fluorine Bond Formation

et al. 2021

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Organocatalyzed Asymmetric Dearomative [3+2] Annulation of Electron‐Deficient 2‐Nitrobenzo Heteroarenes with 3‐Isothiocyanato Oxindoles

et al. 2021

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An organocatalyzed asymmetric dearomative [3+2] annulation reaction of electron‐deficient 2‐nitrobenzo heteroarenes including 2‐nitrobenzofurans, 2‐nitrobenzothiophenes and 2‐nitroindoles with 3‐isothiocyanato oxindoles was developed. With a multiple hydrogen‐bonding bifunctional thiourea as the catalyst, the reaction displays broad substrate scope and provides an access to structurally diverse polycyclic spirooxindoles containing three contiguous stereogenic centers in high yields with good diastereo‐ and enantioselectivities (up to 99% yield, 94:6 dr, and 97% ee). This organocatalysis protocol is able to afford the products with complementarily diastereoselectivity versus the previous work with transition metal catalysis.

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