Novel synthesis of monofluorocyclobutanes by the ring expansion- fluorination of cyclopropylmethanols with an amine-metal fluoride pyridinium poly(hydrogen fluoride)-complex

Kanemoto, Shigekazu; Shimizu, Makoto; Yoshioka, Hirosuke

doi:10.1016/s0040-4039(01)91361-9

Cited by 25 publications

(7 citation statements)

References 13 publications

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“…Glucose-6-phosphate and NADP(H) were purchased from Sigma-Aldrich-Fluka. Sulfides 1, 2, 4, 7, 8,10,14,15,17,18,19, racemic sulfoxides (±)-1a, (±)-7a, (±)-14a, phenylboronic acid 27 and phenol 28 were purchased from Sigma-AldrichFluka. Phenyl sulfides 11, 16 and benzyl sulfides 20-21 were products from Lancaster.…”

Section: Generalmentioning

confidence: 99%

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4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides

Gonzalo

Pazmiño

Ottolina

et al. 2006

Tetrahedron: Asymmetry

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Abstract-Recombinant 4-hydroxyacetophenone monooxygenase (HAPMO) from Pseudomonas fluorescens ACB has been tested as a catalyst in sulfoxidation reactions on a set of aromatic sulfides. With a few exceptions, excellent enantioselectivities in the synthesis of chiral phenyl and benzyl sulfoxides were achieved. The bacterial Baeyer-Villiger monooxygenase was also shown to accept racemic sulfoxides, a prochiral diketone and an organoboron compound as substrates. This study demonstrates the great biocatalytic potential of this novel oxidative enzyme.

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Section: Generalmentioning

confidence: 99%

“…Diketone 29 was purchased by TCI Europe. Sulfides 3, 15 5, 15 20-24, 16 25-26 15 and compound (±)-30 17 were synthesized according to the literature. Sulfoxides were prepared by chemical oxidation from the corresponding sulfides and exhibited physical and spectral properties in agreement with those reported.…”

Section: Generalmentioning

confidence: 99%

4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides

Gonzalo

Pazmiño

Ottolina

et al. 2006

Tetrahedron: Asymmetry

View full text Add to dashboard Cite

show abstract

“…Sulfides 1, 2, 4, 7, 8,10,14,15,17,18,19, racemic sulfoxides (±)-1a, (±)-7a, (±)-14a, phenylboronic acid 27 and phenol 28 were purchased from Sigma-Aldrich-Fluka. Phenyl sulfides 11, 16 and benzyl sulfides 20-21 were products from Lancaster.…”

Section: Generalmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

4‐Hydroxyacetophenone Monooxygenase from Pseudomonas fluorescens ACB as an Oxidative Biocatalyst in the Synthesis of Optically Active Sulfoxides.

et al. 2006

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Sulfoxides Q 0600 4-Hydroxyacetophenone Monooxygenase from Pseudomonas fluorescens ACB as an Oxidative Biocatalyst in the Synthesis of Optically Active Sulfoxides. -The enzyme catalyzes effectively the oxidation of sulfides to sulfoxides, mostly with high yields and excellent enantioselectivities. -(DE GONZALO*, G.; TORRES PAZMINO, D. E.; OTTOLINA, G.; FRAAIJE, M. W.; CARREA, G.; Tetrahedron: Asymmetry 17 (2006) 1, 130-135; Ist. Chim. Riconoscimento Mol., CNR, I-20131 Milano, Italy; Eng.) -Y. Steudel 24-090

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“…In this regard, both ring‐opening and ring‐expanding fluorination reactions of cyclopropane derivatives have emerged as efficient and powerful tools for diverse fluorinated molecules synthesis, such as 1,3‐difluoroalkanes, [8] monofluoroalkenes, [9] functionalized monofluoroalkanes, [10] and others [11] . In the synthesis of homoallylic monofluorides, Yoshioka and coworkers reported a ring‐opening fluorination of cyclopropylmethanols using a combination of HF⋅Py, diisopropylamine, and KHF 2 [12] . This reaction involved the Julia‐Bruylants cyclopropyl carbinol rearrangement, providing homoallylic monofluorides as stereoisomers in certain cases (Scheme 1a, top).…”

Section: Introductionmentioning

confidence: 99%

Divergent Fluorinations of Vinylcyclopropanes: Ring‐Opening 1,5‐Hydrofluorination and Ring‐Retaining 1,2‐Difluorination

Yang

Lin

et al. 2023

Chemistry An Asian Journal

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Organofluorine compounds have been widely used in pharmaceutical, agrochemical, and material sciences. Reported herein are divergent fluorination reactions of vinylcyclopropanes with different electrophiles, which allow the facile synthesis of homoallylic monofluorides and vicinal‐difluorides through ring‐opening 1,5‐hydrofluorination and ring‐retaining 1,2‐difluorination, respectively. Both protocols feature mild conditions, simple operations, good functional group tolerance, and generally good yields. The practicality of these reactions is demonstrated by their scalability, as well as the successful conversion of the formed homoallylic monofluorides into other complex fluorinated molecules.

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Novel synthesis of monofluorocyclobutanes by the ring expansion- fluorination of cyclopropylmethanols with an amine-metal fluoride pyridinium poly(hydrogen fluoride)-complex

Cited by 25 publications

References 13 publications

4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides

4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides

4‐Hydroxyacetophenone Monooxygenase from Pseudomonas fluorescens ACB as an Oxidative Biocatalyst in the Synthesis of Optically Active Sulfoxides.

Divergent Fluorinations of Vinylcyclopropanes: Ring‐Opening 1,5‐Hydrofluorination and Ring‐Retaining 1,2‐Difluorination

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