ChemInform Abstract: Enantioselective Fluorination of α‐Branched Aldehydes and Subsequent Conversion to α‐Hydroxyacetals via Stereospecific C—F Bond Cleavage.

Shibatomi, Kazutaka; Kitahara, Kazumasa; Okimi, Takuya; Abe, Yoshiyuki; Iwasa, Seiji

doi:10.1002/chin.201623027

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“…By 2016, the Shibatomi group reported the enantioselective fluorination of α-branched aldehydes 123 to introduce a fluorine atom onto a tertiary carbon center catalyzed by the chiral primary amine C15 (Scheme 31). 153 Although similar catalyst structure had already been designed in 1996, 154 there was no research related to its applications. Additionally, the steric hindrance of aryl substituent (Ar = 3,5-tBuC 6 H 3 ) in 3,3′-positions on the binaphthyl backbone of the primary amine catalysis exerted impact on the asymmetric induction because employing catalysts without aryl substituents (replacement Ar group by H) in 3,3′positions provided nearly racemic products.…”

Section: Marketed Drugs Featuring Quaternary C−fmentioning

confidence: 99%

Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs

et al. 2018

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New methods for preparation of tailor-made fluorine-containing compounds are in extremely high demand in nearly every sector of chemical industry. The asymmetric construction of quaternary C−F stereogenic centers is the most synthetically challenging and, consequently, the least developed area of research. As a reflection of this apparent methodological deficit, pharmaceutical drugs featuring C−F stereogenic centers constitute less than 1% of all fluorine-containing medicines currently on the market or in clinical development. Here we provide a comprehensive review of current research activity in this area, including such general directions as asymmetric electrophilic fluorination via organocatalytic and transition-metal catalyzed reactions, asymmetric elaboration of fluorine-containing substrates via alkylations, Mannich, Michael, and aldol additions, cross-coupling reactions, and biocatalytic approaches. CONTENTS

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Section: Marketed Drugs Featuring Quaternary C−fmentioning

confidence: 99%

Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs

et al. 2018

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Enantioselective Fluorination of α‐Branched Aldehydes and Subsequent Conversion to α‐Hydroxyacetals via Stereospecific C—F Bond Cleavage.

Abstract: Due to difficulties in purification of intermediate fluorinated aldehydes, subsequent reduction to alcohols or stereospecific conversion to α‐hydroxyacetals in a one‐pot fashion is conducted.

Cited by 1 publication

References 1 publication

Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs

Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs

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