Montmorillonite K 10 (clay) catalyzed hydrolysis of aryl-substituted α,β-difluoroallyl alcohols leading to (Z)-α-fluoro-β-aryl-substituted acrylaldehydes

Funabiki, Kazumasa; Murata, Eiji; Fukushima, Yoshitaka; Matsui, Masaki; Shibata, Katsuyoshi

doi:10.1016/s0040-4020(99)80001-5

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Cited by 10 publications

(2 citation statements)

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“…Montmorillonite K 10 (Clay, MK10) is not effective for the ethanolysis of the allyl alcohol 2a (Table 2, entry 1) at all. 11 It should be noted that only (Z)-isomer was obtained in the all cases.…”

Section: Grignard Reagentsmentioning

confidence: 94%

CFC- or HFC-Free Approach to α-Substituted β,γ,γ-Trifluoroallyl Alcohols by the Reaction of β-Fluoro-β-trifluoromethylated Enol Tosylate with Grignard Reagents

Funabiki¹,

Sawa²,

Shibata³

et al. 2002

Synlett

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Section: Grignard Reagentsmentioning

confidence: 94%

CFC- or HFC-Free Approach to α-Substituted β,γ,γ-Trifluoroallyl Alcohols by the Reaction of β-Fluoro-β-trifluoromethylated Enol Tosylate with Grignard Reagents

Funabiki¹,

Sawa²,

Shibata³

et al. 2002

Synlett

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“…The corresponding 2-fluoropropenal is obtained by mild oxidation of the corresponding alcohol, using for example the tetrapropylammonium perruthenate/ N -methylmorpholine- N -oxide (TPAP/NMO) system or Dess–Martin reagent. There are few syntheses leading directly to the aldehyde, and they use even harsher conditions, which are not compatible with functionalized molecules . We were confronted with this problem during the synthesis the O -glucoside of fluoroconiferyl alcohol, ( Z )-β-fluoroconiferin, a strong inhibitor of lignin polymerization .…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo-β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols

et al. 2011

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We report here the stereoconvergent formylation of (E/Z)-β-bromo-β-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-α-fluorocinnamaldehydes in good yields. The reaction was extended to styrenes bearing electro-attracting or electro-donating groups. The obtained α-fluoroaldehydes were smoothly reduced to the corresponding (Z)-β-fluorocinnamic alcohol by NaBH(4). The reaction could be performed on functionalized substrates as demonstrated by the access to the glucoside of β-fluoroconiferyl alcohol, (Z)-β-fluoroconiferin, a strong inhibitor of lignin polymerization.

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ChemInform Abstract: Montmorillonite K‐10 (Clay) Catalyzed Hydrolysis of Aryl‐Substituted α,β‐Difluoroallyl Alcohols Leading to (Z)‐α‐Fluoro‐β‐aryl‐Substituted Acrylaldehydes.

et al. 1999

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Montmorillonite K 10 (clay) catalyzed hydrolysis of aryl-substituted α,β-difluoroallyl alcohols leading to (Z)-α-fluoro-β-aryl-substituted acrylaldehydes

Cited by 10 publications

References 39 publications

CFC- or HFC-Free Approach to α-Substituted β,γ,γ-Trifluoroallyl Alcohols by the Reaction of β-Fluoro-β-trifluoromethylated Enol Tosylate with Grignard Reagents

CFC- or HFC-Free Approach to α-Substituted β,γ,γ-Trifluoroallyl Alcohols by the Reaction of β-Fluoro-β-trifluoromethylated Enol Tosylate with Grignard Reagents

Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo-β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols

ChemInform Abstract: Montmorillonite K‐10 (Clay) Catalyzed Hydrolysis of Aryl‐Substituted α,β‐Difluoroallyl Alcohols Leading to (Z)‐α‐Fluoro‐β‐aryl‐Substituted Acrylaldehydes.

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