A general, enantioselective synthesis of β- and γ-fluoroamines

O’Reilly, Matthew C.; Lindsley, Craig W.

doi:10.1016/j.tetlet.2013.04.116

Cited by 12 publications

(16 citation statements)

References 23 publications

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“…Simple reductive amination is sufficient to achieve this goal, [65] but there are other methods available. [66][67][68] The synthetic pathway of O'Reilly and Lindsley utilized βfluoroalcohols as key intermediates. These were synthesized from aldehydes by fluorination via MacMillan's method followed by reduction.…”

Section: Fluorination Of Aldehydesmentioning

confidence: 99%

“…α‐Fluoroaldehydes are highly reactive and versatile synthetic intermediates [65–70] . For example, they can be transformed into β‐fluoroamines.…”

Section: Asymmetric C−f Bond‐forming Reactions Using Organocatalysismentioning

confidence: 99%

“…For example, they can be transformed into β‐fluoroamines. Simple reductive amination is sufficient to achieve this goal, [65] but there are other methods available [66–68] . The synthetic pathway of O'Reilly and Lindsley utilized β‐fluoroalcohols as key intermediates.…”

Section: Asymmetric C−f Bond‐forming Reactions Using Organocatalysismentioning

confidence: 99%

“…Replacement of the amine with KCN yielded β‐fluorocyanides, which could be reduced with InCl 3 /NaBH 4 to deliver chiral γ‐fluoroamines (other reducing methods cause serious decomposition or defluorination). Scheme 30 shows examples of the above reactions [66] …”

Section: Asymmetric C−f Bond‐forming Reactions Using Organocatalysismentioning

confidence: 99%

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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: Fluorination Of Aldehydesmentioning

confidence: 99%

“…α‐Fluoroaldehydes are highly reactive and versatile synthetic intermediates [65–70] . For example, they can be transformed into β‐fluoroamines.…”

Section: Asymmetric C−f Bond‐forming Reactions Using Organocatalysismentioning

confidence: 99%

Section: Asymmetric C−f Bond‐forming Reactions Using Organocatalysismentioning

confidence: 99%

Section: Asymmetric C−f Bond‐forming Reactions Using Organocatalysismentioning

confidence: 99%

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Asymmetric Methods for Carbon‐Fluorine Bond Formation

et al. 2021

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“…On the basis of the interest in fluorine-containing amines, 14 we began our investigation by examining the fluoroarylation of protected allylamine 1a with phenylboronic acid ( 2a ). Using these substrates, conditions similar to those previously employed in the 1,2-fluoroarylation of styrenes 10 afforded the 1,1-fluoroarylation product 3a , albeit with moderate yield ( Table 1 , entry 1).…”

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confidence: 99%

Palladium-Catalyzed Enantioselective 1,1-Fluoroarylation of Aminoalkenes

et al. 2015

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The development of an enantioselective palladium-catalyzed 1,1-fluoroarylation of unactivated aminoalkenes is described. The reaction uses arylboronic acids as the arene source and Selectfluor as the fluorine source to generate benzylic fluorides in good yields with excellent enantioselectivities. This transformation, likely proceeding through an oxidative Heck mechanism, affords 1,1-difunctionalized alkene products.

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