Synthesis of Chiral Menthoxymethyl Ether of Phenol and Substituted Phenol and their Use in Directed Ortho Metalation

Mumtaz, Salma; Khan, Sher Wali; Zaidi, J. H.; Iqbal, Anila; Cheema, Zain Maqsood; Khan, Khalid Mohammed; Perveen, Shahnaz

doi:10.2174/15701786113109990020

Cited by 6 publications

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“…To explore the substrate scope of this reaction, optimized conditions were employed to structurally different bis -alkoxy methanes ( 1a – j , see Additional file 1 ) [ 33 ]. The method was found equally efficient to obtain broad range of alkoxymethylphosphonium iodides ( 2a – j , Table 2 ) based on primary, secondary, tertiary and benzylic alkoxy groups.…”

Section: Resultsmentioning

confidence: 99%

Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Gondal

Cheema

Zaidi

et al. 2018

Chemistry Central Journal

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An efficient one pot method for the synthesis of α-alkoxymethylphosphonium iodides is developed by using PPh3/I2 combination at room temperature. Reaction conditions are found general to synthesize wide range of structurally variant alkoxymethylphosphonium iodides in high yield (70–91%). These new functionalized phosphonium salts are further used in stereoselective synthesis of vinyl ethers as well as in carbon homologation of aldehydes.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0421-6) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Gondal

Cheema

Zaidi

et al. 2018

Chemistry Central Journal

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“…To study the substrate scope, structurally variant bisalkoxymethanes (1b-e) were synthesized by reported method [39,40]. The optimized reaction conditions were found equally effective for primary, secondary and even tertiary alkoxy groups (Table 2).…”

Section: 2 Results and Discussionmentioning

confidence: 99%

Facile Efficient Synthesis of New Alkoxymethylphosphonium Tetrafluoroborates; Valuable Alternative to Their Halide Analogues

et al. 2018

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“…The reaction of paraformaldehyde with the chiral alcohols 1a-c generated the corresponding acetals 2a-c, which were reacted in situ with acetyl chloride to give the alkoxymethyl halides 3a-c (Scheme 1a). 16 Next, the non-racemic ILs 4a-c were synthesized in good yields (Scheme 1b) by reaction of 3a-c with 1-methylbenzimidazole at room temperature (RT). This step is very fast since the reaction mixture was immediately transformed in a semisolid which was further stirred for 30 min to ensure the complete reaction.…”

Section: Synthesis and Characterization Of The New Benzimidazoliumbasmentioning

confidence: 99%

Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates

Mumtaz

Cano

Mumtaz

et al. 2018

Phys. Chem. Chem. Phys.

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A series of novel benzimidazolium-based non-racemic ionic liquids (ILs) was synthesized from low-cost chiral terpenoid alcohols and fully characterized by the use of a wide variety of techniques, such as DSC, ESI-MS, ATR FT-IR, polarimetry as well as 1H and 13C NMR spectroscopy. The ILs were investigated as chiral shift agents for the chiral recognition of racemic mixtures of Mosher's acid potassium salt by 19F NMR spectroscopy, leading to high splitting values of the CF3 signal. Supramolecular interactions between salt and H-C2 of chiral benzimidazolium cation are responsible for the chiral recognition, as was demonstrated by experimental evidences. Indeed, the enantiomeric excess value of enantioenriched substrates depends mainly on the strength of the contact ion pairs.

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Synthesis of Chiral Menthoxymethyl Ether of Phenol and Substituted Phenol and their Use in Directed Ortho Metalation

Cited by 6 publications

References 0 publications

Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Facile Efficient Synthesis of New Alkoxymethylphosphonium Tetrafluoroborates; Valuable Alternative to Their Halide Analogues

Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates

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