Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines

Julia A. Kalow; Dana E. Schmitt; Abigail G. Doyle

doi:10.1021/jo300433a

Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines

Julia A. Kalow, Dana E. Schmitt, Abigail G. Doyle

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92 Scopus citations

Abstract

Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide β-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.

Original language	English (US)
Pages (from-to)	4177-4183
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	77
Issue number	8
DOIs	https://doi.org/10.1021/jo300433a
State	Published - Apr 20 2012

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo300433a

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abstract = "Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide β-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.",

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journal = "Journal of Organic Chemistry",

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AU - Kalow, Julia A.

AU - Schmitt, Dana E.

AU - Doyle, Abigail G.

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Y1 - 2012/4/20

N2 - Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide β-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.

AB - Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide β-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.

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M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

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Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines

Abstract

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