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A. K. Basak - One of the best experts on this subject based on the ideXlab platform.
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Dess-Martin Periodinane Promoted Oxidative Coupling of Baylis-Hillman Adducts with Silyl Enol Ethers: A Novel Synthesis of cis-Fused Dihydropyrans
Synlett, 2008Co-Authors: Jhillu S. Yadav, Sourav Mandal, C. Madavi, B. V. Subba Reddy, A. K. Basak, A. C. KunwarAbstract:Baylis-Hillman adducts undergo smooth oxidative Mukaiyama-Michael addition and a subsequent cyclization with silyl enol ethers in the presence of Dess-Martin Periodinane (DMP) and pyridine under mild reaction conditions to afford a new class of dihydropyran derivatives in good yields with high diastereoselectivity. This is the first report on the preparation of cis-fused dihydropyrans from Baylis-Hillman adducts and silyl enol ethers.
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One-Pot Oxidative Allylation of Morita-Baylis-Hillman Adducts with Allyltrimethylsilane Promoted by Dess-Martin Periodinane/Boron Trifluoride-Diethyl Ether Complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, B. V. Subba Reddy, Ashutosh Pratap Singh, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with allyltrimethylsilane in the presence of Dess-Martin Periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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one pot oxidative allylation of morita baylis hillman adducts with allyltrimethylsilane promoted by Dess Martin Periodinane boron trifluoride diethyl ether complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, Ashutosh Pratap Singh, B Subba V Reddy, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with allyltrimethylsilane in the presence of Dess-Martin Periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents
Tetrahedron, 2004Co-Authors: Jhillu S. Yadav, A. K. Basak, B. V. S. Reddy, A. Venkat NarsaiahAbstract:Abstract Alcohols undergo smooth oxidation with iodoxybenzoic acid (IBX) or with Dess–Martin-Periodinane (DMP) in hydrophilic [bmim]BF4 and hydrophobic [bmim]PF6 ionic liquids at room temperature under mild conditions to afford the corresponding carbonyl compounds in excellent yields with high selectivity. IBX and DMP promoted oxidations are faster in ionic liquids when compared to conventional solvents such as DMSO, DMF, EtOAc and H2O. The recovery of the byproduct iodosobenzoic acid (IBA) is especially simple in ionic liquids. The recovered ionic liquids can be recycled in subsequent reactions with consistent activity.
Jhillu S. Yadav - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of (+)-lycoricidine by the application of oxidative and regioselective ring-opening of aziridines.
Organic Letters, 2010Co-Authors: Jhillu S. Yadav, G. Satheesh, Changalvala V. S. R. MurthyAbstract:A highly stereoselective total synthesis of (+)-lycoricidine has been described. The salient features of this synthesis are the one-pot elimination followed by allylation reaction, ring-closing metathesis, stereoselective aziridine formation, Dess−Martin Periodinane, and silica gel mediated oxidative ring-opening of aziridine to form α,β-unsaturated ketone (allyl amine) and intramolecular Heck cyclization.
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Dess-Martin Periodinane Promoted Oxidative Coupling of Baylis-Hillman Adducts with Silyl Enol Ethers: A Novel Synthesis of cis-Fused Dihydropyrans
Synlett, 2008Co-Authors: Jhillu S. Yadav, Sourav Mandal, C. Madavi, B. V. Subba Reddy, A. K. Basak, A. C. KunwarAbstract:Baylis-Hillman adducts undergo smooth oxidative Mukaiyama-Michael addition and a subsequent cyclization with silyl enol ethers in the presence of Dess-Martin Periodinane (DMP) and pyridine under mild reaction conditions to afford a new class of dihydropyran derivatives in good yields with high diastereoselectivity. This is the first report on the preparation of cis-fused dihydropyrans from Baylis-Hillman adducts and silyl enol ethers.
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One-Pot Oxidative Allylation of Morita-Baylis-Hillman Adducts with Allyltrimethylsilane Promoted by Dess-Martin Periodinane/Boron Trifluoride-Diethyl Ether Complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, B. V. Subba Reddy, Ashutosh Pratap Singh, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with allyltrimethylsilane in the presence of Dess-Martin Periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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one pot oxidative allylation of morita baylis hillman adducts with allyltrimethylsilane promoted by Dess Martin Periodinane boron trifluoride diethyl ether complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, Ashutosh Pratap Singh, B Subba V Reddy, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with allyltrimethylsilane in the presence of Dess-Martin Periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents
Tetrahedron, 2004Co-Authors: Jhillu S. Yadav, A. K. Basak, B. V. S. Reddy, A. Venkat NarsaiahAbstract:Abstract Alcohols undergo smooth oxidation with iodoxybenzoic acid (IBX) or with Dess–Martin-Periodinane (DMP) in hydrophilic [bmim]BF4 and hydrophobic [bmim]PF6 ionic liquids at room temperature under mild conditions to afford the corresponding carbonyl compounds in excellent yields with high selectivity. IBX and DMP promoted oxidations are faster in ionic liquids when compared to conventional solvents such as DMSO, DMF, EtOAc and H2O. The recovery of the byproduct iodosobenzoic acid (IBA) is especially simple in ionic liquids. The recovered ionic liquids can be recycled in subsequent reactions with consistent activity.
Ashutosh Pratap Singh - One of the best experts on this subject based on the ideXlab platform.
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One-Pot Oxidative Allylation of Morita-Baylis-Hillman Adducts with Allyltrimethylsilane Promoted by Dess-Martin Periodinane/Boron Trifluoride-Diethyl Ether Complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, B. V. Subba Reddy, Ashutosh Pratap Singh, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with allyltrimethylsilane in the presence of Dess-Martin Periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
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one pot oxidative allylation of morita baylis hillman adducts with allyltrimethylsilane promoted by Dess Martin Periodinane boron trifluoride diethyl ether complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, Ashutosh Pratap Singh, B Subba V Reddy, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with allyltrimethylsilane in the presence of Dess-Martin Periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
B. V. Subba Reddy - One of the best experts on this subject based on the ideXlab platform.
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Dess-Martin Periodinane Promoted Oxidative Coupling of Baylis-Hillman Adducts with Silyl Enol Ethers: A Novel Synthesis of cis-Fused Dihydropyrans
Synlett, 2008Co-Authors: Jhillu S. Yadav, Sourav Mandal, C. Madavi, B. V. Subba Reddy, A. K. Basak, A. C. KunwarAbstract:Baylis-Hillman adducts undergo smooth oxidative Mukaiyama-Michael addition and a subsequent cyclization with silyl enol ethers in the presence of Dess-Martin Periodinane (DMP) and pyridine under mild reaction conditions to afford a new class of dihydropyran derivatives in good yields with high diastereoselectivity. This is the first report on the preparation of cis-fused dihydropyrans from Baylis-Hillman adducts and silyl enol ethers.
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One-Pot Oxidative Allylation of Morita-Baylis-Hillman Adducts with Allyltrimethylsilane Promoted by Dess-Martin Periodinane/Boron Trifluoride-Diethyl Ether Complex
Synthesis, 2008Co-Authors: Jhillu S. Yadav, B. V. Subba Reddy, Ashutosh Pratap Singh, A. K. BasakAbstract:Morita-Baylis-Hillman adducts undergo smooth one-pot oxidative conjugate addition with allyltrimethylsilane in the presence of Dess-Martin Periodinane/boron trifluoride-diethyl ether complex under mild reaction conditions to afford various homoallylated β-keto ester derivatives in good yields with high 1,4-selectivity.
Andrea Buettner - One of the best experts on this subject based on the ideXlab platform.
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syntheses of chiral 1 8 cineole metabolites and determination of their enantiomeric composition in human urine after ingestion of 1 8 cineole containing capsules
ChemPlusChem, 2013Co-Authors: Monika Schaffarczyk, Teodor Silviu Balaban, Michael Rychlik, Andrea BuettnerAbstract:The chiral metabolites in human urine were investigated after ingestion of a 1,8-cineole (eucalyptol)-containing entero-coated capsule (Soledum). For identification of the various enantiomers the enantiomerically pure (−/+)-α2-hydroxy-1,8-cineole, (−/+)-β2-hydroxy-1,8-cineole, (−/+)-9-hydroxy-1,8-cineole, and (−/+)-2-oxo-1,8-cineole were prepared. To achieve this aim, after acetylation of the synthesized racemic 2- and 9-hydroxy-1,8-cineoles, pig liver esterase- or yeast-mediated hydrolysis provided the (−)-alcohols with their antipodal (+)-acetates with enantiomeric excess of 33–100 %. Dess–Martin Periodinane oxidation of the alcohol (+)-α2-hydroxy-1,8-cineole, obtained by hydrolysis of the resolved acetate, provided the corresponding (+)-2-oxo-1,8-cineole, meanwhile the oxidation of (−)-α2-hydroxy-1,8-cineole gave (−)-2-oxo-1,8-cineole. Using these standards seven metabolites (+/−)-α2-hydroxy-1,8-cineole, (+/−)-β2-hydroxy-1,8-cineole, (+/−)-α3-hydroxycineole, (+/−)-3-oxo-1,8-cineole, 4-hydroxy-1,8-cineole, 7-hydroxy-1,8-cineole, and (+/−)-9-hydroxy-1,8-cineole, all liberated from their glucuronides, were identified in urine by GC-MS on a chiral stationary phase after consumption of 100 mg of 1,8-cineole. Metabolite screening using 2H3-1,8-cineol as the internal standard revealed (+/−)-α2-hydroxy-1,8-cineole as the predominant metabolite followed by (+/−)-9-hydroxy-1,8-cineole. Furthermore, the results showed that one enantiomer is always formed preferentially.