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Stephanie Corsi - One of the best experts on this subject based on the ideXlab platform.
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one pot three step thioconjugate addition oxidation diels alder reactions of Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: Wade C Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Stephanie CorsiAbstract:Ethyl Propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
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One-pot synthesis of (Z)-β-sulfonyl enoates from Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Brian C. Southall, Stephanie Corsi, Eric W. Etchill, Ryan J. SaultAbstract:Abstract β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from Ethyl Propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of aliphatic thiols. Addition of meta-chloroperbenzoic acid (mCPBA) and LiClO4 to the reaction mixture provides rapid access to the sulfonyl enoates. Yields of the pure Z isomer range from 51–90%.
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One-pot three-step thioconjugate addition-oxidation-Diels–Alder reactions of Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Stephanie CorsiAbstract:Ethyl Propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
Yao-ling Qiu - One of the best experts on this subject based on the ideXlab platform.
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preliminary notedirect hydroperfluoroalkylation of Ethyl Propiolate with perfluoroalkyl iodides and bromides by a co zn bimetal redox system
Journal of Fluorine Chemistry, 1991Co-Authors: Yao-ling QiuAbstract:The addition of perfluoroalkyl halides RfX (1) (X=I, Br) to Ethyl Propiolate (2) has been performed smoothly with zinc powder and a catalytic amount of bromo(pyridine)cobaloxime(III) (3) in ethanol. The product (4) was a mixture of Z- and E-isomers, with the former predominating.
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Direct hydroperfluoroalkylation of Ethyl Propiolate with perfluoroalkyl iodides and bromides by a Co/Zn bimetal redox system
Journal of Fluorine Chemistry, 1991Co-Authors: Yao-ling QiuAbstract:Abstract The addition of perfluoroalkyl halides R f X ( 1 ) (X=I, Br) to Ethyl Propiolate ( 2 ) has been performed smoothly with zinc powder and a catalytic amount of bromo(pyridine)cobaloxime(III) ( 3 ) in ethanol. The product ( 4 ) was a mixture of Z - and E -isomers, with the former predominating.
Ana M. Neferu - One of the best experts on this subject based on the ideXlab platform.
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one pot three step thioconjugate addition oxidation diels alder reactions of Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: Wade C Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Stephanie CorsiAbstract:Ethyl Propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
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One-pot synthesis of (Z)-β-sulfonyl enoates from Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Brian C. Southall, Stephanie Corsi, Eric W. Etchill, Ryan J. SaultAbstract:Abstract β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from Ethyl Propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of aliphatic thiols. Addition of meta-chloroperbenzoic acid (mCPBA) and LiClO4 to the reaction mixture provides rapid access to the sulfonyl enoates. Yields of the pure Z isomer range from 51–90%.
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One-pot three-step thioconjugate addition-oxidation-Diels–Alder reactions of Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Stephanie CorsiAbstract:Ethyl Propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
Carly J. Mueller - One of the best experts on this subject based on the ideXlab platform.
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one pot three step thioconjugate addition oxidation diels alder reactions of Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: Wade C Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Stephanie CorsiAbstract:Ethyl Propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
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One-pot synthesis of (Z)-β-sulfonyl enoates from Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Brian C. Southall, Stephanie Corsi, Eric W. Etchill, Ryan J. SaultAbstract:Abstract β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from Ethyl Propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of aliphatic thiols. Addition of meta-chloroperbenzoic acid (mCPBA) and LiClO4 to the reaction mixture provides rapid access to the sulfonyl enoates. Yields of the pure Z isomer range from 51–90%.
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One-pot three-step thioconjugate addition-oxidation-Diels–Alder reactions of Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Stephanie CorsiAbstract:Ethyl Propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
Smaranda Craciun - One of the best experts on this subject based on the ideXlab platform.
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one pot three step thioconjugate addition oxidation diels alder reactions of Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: Wade C Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Stephanie CorsiAbstract:Ethyl Propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
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One-pot synthesis of (Z)-β-sulfonyl enoates from Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Brian C. Southall, Stephanie Corsi, Eric W. Etchill, Ryan J. SaultAbstract:Abstract β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from Ethyl Propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of aliphatic thiols. Addition of meta-chloroperbenzoic acid (mCPBA) and LiClO4 to the reaction mixture provides rapid access to the sulfonyl enoates. Yields of the pure Z isomer range from 51–90%.
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One-pot three-step thioconjugate addition-oxidation-Diels–Alder reactions of Ethyl Propiolate
Tetrahedron Letters, 2012Co-Authors: C. Wade Downey, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Stephanie CorsiAbstract:Ethyl Propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.