Improving Enantioselective Fluorination Reactions: Chiral N-Fluoroammonium Salts and Transition Metal Catalysts

Muñiz, Kilian

doi:10.1002/1521-3773(20010504)40:9<1653::aid-anie16530>3.3.co;2-n

Cited by 5 publications

(5 citation statements)

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“…Selectfluor (1) has been used to transfer fluorine onto various cinchona alkaloids to generate chiral electrophilic fluorination reagents. 41 The first enantioselective fluorinating reagent, the N-fluoro quaternary ammonium salt of cinchonidine, was prepared in a one-step transfer-fluorination of the quinuclidine moiety with 1 (Scheme 19). 42 The X-ray crystal structure showed the N-F distance is 1.409(7) Å, which approaches that found in other N-F electrophilic fluorinating reagents.…”

Section: Stereoselective Electrophilic Fluorination Reactionsmentioning

confidence: 99%

“…A. Syntheses of Chiral N − F Reagents and Their Uses in Asymmetric Syntheses. Selectfluor ( 1 ) has been used to transfer fluorine onto various cinchona alkaloids to generate chiral electrophilic fluorination reagents . The first enantioselective fluorinating reagent, the N-fluoro quaternary ammonium salt of cinchonidine, was prepared in a one-step transfer-fluorination of the quinuclidine moiety with 1 (Scheme ) .…”

Section: Stereoselective Electrophilic Fluorination Reactionsmentioning

confidence: 99%

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Recent Highlights in Electrophilic Fluorination with 1-Chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)

2003

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Synthetic and structural aspects of organofluorine compounds continue to be the focal points of vigorous research activities, as evidenced by the appearance of a large number of publications. Among the various useful methodologies for the introduction of fluorine into organic molecules, electrophilic fluorination is a promising and exciting area of research. While a variety of electrophilic fluorinating reagents are available, currently 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) provides a remarkably straightforward and effective route. The breadth of applications realizable from this reagent in its role as a key electrophilic fluorinating reagent is highlighted here. This Account covers the literature for electrophilic fluorination reactions that employ Selectfluor during the period January 1999-January 2003.

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Section: Stereoselective Electrophilic Fluorination Reactionsmentioning

confidence: 99%

Section: Stereoselective Electrophilic Fluorination Reactionsmentioning

confidence: 99%

Recent Highlights in Electrophilic Fluorination with 1-Chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)

2003

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“…The introduction of fluorine atom into organic molecules is of considerable significance in pharmaceuticals, agrochemicals, and material sciences . Because of the acidic α ‐H of the ketone, α ‐fluorinated ketones are easy to access . In contrast, the synthesis of distal (β, γ, δ, etc.)…”

Section: Ring‐opening Strategy For the Synthesis Of Distally Substitumentioning

confidence: 99%

Recent Advances in Ring‐Opening Functionalization of Cycloalkanols by C–C σ‐Bond Cleavage

Zhu

2018

The Chemical Record

131

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Cycloalkanols prove to be privileged precursors for the synthesis of distally substituted alkyl ketones and polycyclic aromatic hydrocarbons (PAHs) by virtue of cleavage of their cyclic C-C bonds. Direct functionalization of cyclobutanols to build up other chemical bonds (e. g., C-F, C-Cl, C-Br, C-N, C-S, C-Se, C-C, etc.) has been achieved by using the ring-opening strategy. Mechanistically, the C-C cleavage of cyclobutanols can be involved in two pathways: (a) transition-metal catalyzed β-carbon elimination; (b) radical-mediated 'radical clock'-type ring opening. The recent advances of our group for the ring-opening functionalization of tertiary cycloalkanols are described in this account.

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“…In recent years, the enantioselective electrophilic halogenation of carbonyl compounds as one of the best established strategies for the construction of chiral C-X bonds [4][5][6][7][8] has gained considerable interest in organic chemistry. Based on Lewis acid catalysis [9] or organocatalysis [10,11], several methodologies for the stereocontrolled formation of carbon halogen bonds neighboring to either one or two carbonyl groups have been focused on by many researchers over the past decade.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(II) complexes of squaramide-linked bisoxazoline ligand

Jia

2014

Chinese Chemical Letters

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Improving Enantioselective Fluorination Reactions: Chiral N-Fluoroammonium Salts and Transition Metal Catalysts

Cited by 5 publications

References 0 publications

Recent Highlights in Electrophilic Fluorination with 1-Chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)

Recent Highlights in Electrophilic Fluorination with 1-Chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)

Recent Advances in Ring‐Opening Functionalization of Cycloalkanols by C–C σ‐Bond Cleavage

Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(II) complexes of squaramide-linked bisoxazoline ligand

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