The Experts below are selected from a list of 522 Experts worldwide ranked by ideXlab platform
M Penso - One of the best experts on this subject based on the ideXlab platform.
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regioselective o sulfonylation of n n bis 2 hydroxyalkyl tosylamides as a synthetic key step to enantiopure Morpholines
Organic Letters, 2017Co-Authors: Francesca Foschi, Domenico Albanese, Ilir Pecnikaj, Aaron Tagliabue, M PensoAbstract:The synthesis of enantiopure 2,6-disubstituted Morpholines was realized through sequential ring opening of two different optically pure oxiranes by a tosylamide, under solid–liquid phase-transfer catalysis (SL-PTC) conditions, mono-O-sulfonylation of the resulting tosylamido-2,2′-diol, and cyclization to the morpholine. The crucial step, the regioselective formation of the monosulfonate, was controlled by taking advantage of the different stereo, electronic, and coordination properties of the oxirane-derived side chains in the diol backbone. As an application of this protocol, a new morpholine-3-carboxamide was synthesized starting from threonine.
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Regioselective O‑Sulfonylation of N,N‑Bis(2-hydroxyalkyl)tosylamides as a Synthetic Key Step to Enantiopure Morpholines
2016Co-Authors: Francesca Foschi, Domenico Albanese, Ilir Pecnikaj, Aaron Tagliabue, M PensoAbstract:The synthesis of enantiopure 2,6-disubstituted Morpholines was realized through sequential ring opening of two different optically pure oxiranes by a tosylamide, under solid–liquid phase-transfer catalysis (SL-PTC) conditions, mono-O-sulfonylation of the resulting tosylamido-2,2′-diol, and cyclization to the morpholine. The crucial step, the regioselective formation of the monosulfonate, was controlled by taking advantage of the different stereo, electronic, and coordination properties of the oxirane-derived side chains in the diol backbone. As an application of this protocol, a new morpholine-3-carboxamide was synthesized starting from threonine
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concise synthesis of c 2 symmetrical 2 6 disubstituted Morpholines by n o boc migration under sl ptc conditions
Organic Process Research & Development, 2010Co-Authors: Domenico Albanese, Aaron Tagliabue, M Penso, Dario Landini, Emanuele CarliniAbstract:A novel, straightforward synthesis of enantiomerically pure 2,6-disubstituted Morpholines has been developed. The ring-opening of epoxides with TsNHBoc under solid−liquid phase transfer catalysis c...
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a straightforward synthesisof enantiopure 2 6 disubstituted Morpholines by a regioselectiveo protection activation protocol
Synlett, 2008Co-Authors: M Penso, Francesca Foschi, Domenico Albanese, Vittoria Lupi, Dario Landini, Aaron TagliabueAbstract:: Enantiopure 2,6-disubstituted Morpholines have been synthesized through the ring opening of chiral, nonracemic oxiranes with nitrogen nucleophiles, under solid-liquid phase-transfer catalysis (SL-PTC) conditions. The β-hydroxytosyi amides resulting from the ring opening of a first epoxide with TsNH 2 was used as nucleophile, after protection of the hydroxyl group, in the reaction with a second oxirane. The morpholine skeleton has been generated through standard functional group chemistry, followed by cyclization of the intermediate p-hydroxy-β'-tosyloxy-tosylamides carried out under SL-PTC conditions. N-Tosyl Morpholines produced can be employed as building blocks in the synthesis of pharmaceuticals and as chiral tools.
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practical synthesis of enantiomerically pure Morpholines
Chimica Oggi-chemistry Today, 2008Co-Authors: Domenico Albanese, Francesca Foschi, Aaron Tagliabue, Emanuele Carlini, M PensoAbstract:Recent advances towards the synthesis of enantiomerically pure substituted Morpholines are reported.
J V K Prasad - One of the best experts on this subject based on the ideXlab platform.
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stereoselective synthesis of cis 2 6 disubstituted Morpholines and 1 4 oxathianes by intramolecular reductive etherification of 1 5 diketones
ChemInform, 2015Co-Authors: Santosh J. Gharpure, Dandela Anuradha, J V K PrasadAbstract:A triethylsilane/TmsOTf-mediated reductive etherification is developed to allow the cyclization of diketones of type (I) and (III) to give 2,6-disubstituted Morpholines and 1,4-oxathianes in excellent trans-diastereoselectivity.
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stereoselective synthesis of cis 2 6 disubstituted Morpholines and 1 4 oxathianes by intramolecular reductive etherification of 1 5 diketones
European Journal of Organic Chemistry, 2015Co-Authors: Santosh J. Gharpure, Dandela Anuradha, J V K PrasadAbstract:A simple and efficient, Lewis acid catalysed reductive etherification strategy for the stereoselective synthesis of cis-2,6-disubstituted Morpholines and 1,4-oxathianes starting from readily available 1,5-diketones has been developed. The strategy is used in the total synthesis of morpholine-based natural products (±)-chelonin A and formal total synthesis of (±)-chelonin C.
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stereoselective synthesis of c substituted morpholine derivatives using reductive etherification reaction total synthesis of chelonin c
ChemInform, 2012Co-Authors: Santosh J. Gharpure, J V K PrasadAbstract:A new and stereoselective approach to polysubstituted Morpholines and fused analogues is reported.
David Barker - One of the best experts on this subject based on the ideXlab platform.
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synthesis of 2 3 syn diarylpent 4 enamides via acyl claisen rearrangements of substituted cinnamyl Morpholines application to the synthesis of magnosalicin
ChemInform, 2012Co-Authors: Benjamin D Dickson, Nora Dittrich, David BarkerAbstract:The Lewis acid catalyzed title reaction of allylic Morpholines with substituted acetyl chlorides gives the desired amides (III) in good to excellent yields.
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synthesis of 2 3 syn diarylpent 4 enamides via acyl claisen rearrangements of substituted cinnamyl Morpholines application to the synthesis of magnosalicin
Tetrahedron Letters, 2012Co-Authors: Benjamin D Dickson, Nora Dittrich, David BarkerAbstract:The acyl-Claisen rearrangement of substituted phenylacetyl chlorides and cinnamyl Morpholines gives 2,3-syn-diarylpent-4-enamides. Electron-rich cinnamyl Morpholines containing alkoxy substituents only reacted with phenylacetyl chlorides; replacement of the phenylacetyl chlorides with alkyl acid chlorides in these reactions gave no rearranged products. Use of the morpholine amides generated in the synthesis of the natural tetrahydrofuran neolignan magnosalicin and tetraphenyl tetrahydrofuran is also reported.
Domenico Albanese - One of the best experts on this subject based on the ideXlab platform.
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regioselective o sulfonylation of n n bis 2 hydroxyalkyl tosylamides as a synthetic key step to enantiopure Morpholines
Organic Letters, 2017Co-Authors: Francesca Foschi, Domenico Albanese, Ilir Pecnikaj, Aaron Tagliabue, M PensoAbstract:The synthesis of enantiopure 2,6-disubstituted Morpholines was realized through sequential ring opening of two different optically pure oxiranes by a tosylamide, under solid–liquid phase-transfer catalysis (SL-PTC) conditions, mono-O-sulfonylation of the resulting tosylamido-2,2′-diol, and cyclization to the morpholine. The crucial step, the regioselective formation of the monosulfonate, was controlled by taking advantage of the different stereo, electronic, and coordination properties of the oxirane-derived side chains in the diol backbone. As an application of this protocol, a new morpholine-3-carboxamide was synthesized starting from threonine.
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Regioselective O‑Sulfonylation of N,N‑Bis(2-hydroxyalkyl)tosylamides as a Synthetic Key Step to Enantiopure Morpholines
2016Co-Authors: Francesca Foschi, Domenico Albanese, Ilir Pecnikaj, Aaron Tagliabue, M PensoAbstract:The synthesis of enantiopure 2,6-disubstituted Morpholines was realized through sequential ring opening of two different optically pure oxiranes by a tosylamide, under solid–liquid phase-transfer catalysis (SL-PTC) conditions, mono-O-sulfonylation of the resulting tosylamido-2,2′-diol, and cyclization to the morpholine. The crucial step, the regioselective formation of the monosulfonate, was controlled by taking advantage of the different stereo, electronic, and coordination properties of the oxirane-derived side chains in the diol backbone. As an application of this protocol, a new morpholine-3-carboxamide was synthesized starting from threonine
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concise synthesis of c 2 symmetrical 2 6 disubstituted Morpholines by n o boc migration under sl ptc conditions
Organic Process Research & Development, 2010Co-Authors: Domenico Albanese, Aaron Tagliabue, M Penso, Dario Landini, Emanuele CarliniAbstract:A novel, straightforward synthesis of enantiomerically pure 2,6-disubstituted Morpholines has been developed. The ring-opening of epoxides with TsNHBoc under solid−liquid phase transfer catalysis c...
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a straightforward synthesisof enantiopure 2 6 disubstituted Morpholines by a regioselectiveo protection activation protocol
Synlett, 2008Co-Authors: M Penso, Francesca Foschi, Domenico Albanese, Vittoria Lupi, Dario Landini, Aaron TagliabueAbstract:: Enantiopure 2,6-disubstituted Morpholines have been synthesized through the ring opening of chiral, nonracemic oxiranes with nitrogen nucleophiles, under solid-liquid phase-transfer catalysis (SL-PTC) conditions. The β-hydroxytosyi amides resulting from the ring opening of a first epoxide with TsNH 2 was used as nucleophile, after protection of the hydroxyl group, in the reaction with a second oxirane. The morpholine skeleton has been generated through standard functional group chemistry, followed by cyclization of the intermediate p-hydroxy-β'-tosyloxy-tosylamides carried out under SL-PTC conditions. N-Tosyl Morpholines produced can be employed as building blocks in the synthesis of pharmaceuticals and as chiral tools.
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practical synthesis of enantiomerically pure Morpholines
Chimica Oggi-chemistry Today, 2008Co-Authors: Domenico Albanese, Francesca Foschi, Aaron Tagliabue, Emanuele Carlini, M PensoAbstract:Recent advances towards the synthesis of enantiomerically pure substituted Morpholines are reported.
Aaron Tagliabue - One of the best experts on this subject based on the ideXlab platform.
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regioselective o sulfonylation of n n bis 2 hydroxyalkyl tosylamides as a synthetic key step to enantiopure Morpholines
Organic Letters, 2017Co-Authors: Francesca Foschi, Domenico Albanese, Ilir Pecnikaj, Aaron Tagliabue, M PensoAbstract:The synthesis of enantiopure 2,6-disubstituted Morpholines was realized through sequential ring opening of two different optically pure oxiranes by a tosylamide, under solid–liquid phase-transfer catalysis (SL-PTC) conditions, mono-O-sulfonylation of the resulting tosylamido-2,2′-diol, and cyclization to the morpholine. The crucial step, the regioselective formation of the monosulfonate, was controlled by taking advantage of the different stereo, electronic, and coordination properties of the oxirane-derived side chains in the diol backbone. As an application of this protocol, a new morpholine-3-carboxamide was synthesized starting from threonine.
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Regioselective O‑Sulfonylation of N,N‑Bis(2-hydroxyalkyl)tosylamides as a Synthetic Key Step to Enantiopure Morpholines
2016Co-Authors: Francesca Foschi, Domenico Albanese, Ilir Pecnikaj, Aaron Tagliabue, M PensoAbstract:The synthesis of enantiopure 2,6-disubstituted Morpholines was realized through sequential ring opening of two different optically pure oxiranes by a tosylamide, under solid–liquid phase-transfer catalysis (SL-PTC) conditions, mono-O-sulfonylation of the resulting tosylamido-2,2′-diol, and cyclization to the morpholine. The crucial step, the regioselective formation of the monosulfonate, was controlled by taking advantage of the different stereo, electronic, and coordination properties of the oxirane-derived side chains in the diol backbone. As an application of this protocol, a new morpholine-3-carboxamide was synthesized starting from threonine
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concise synthesis of c 2 symmetrical 2 6 disubstituted Morpholines by n o boc migration under sl ptc conditions
Organic Process Research & Development, 2010Co-Authors: Domenico Albanese, Aaron Tagliabue, M Penso, Dario Landini, Emanuele CarliniAbstract:A novel, straightforward synthesis of enantiomerically pure 2,6-disubstituted Morpholines has been developed. The ring-opening of epoxides with TsNHBoc under solid−liquid phase transfer catalysis c...
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a straightforward synthesisof enantiopure 2 6 disubstituted Morpholines by a regioselectiveo protection activation protocol
Synlett, 2008Co-Authors: M Penso, Francesca Foschi, Domenico Albanese, Vittoria Lupi, Dario Landini, Aaron TagliabueAbstract:: Enantiopure 2,6-disubstituted Morpholines have been synthesized through the ring opening of chiral, nonracemic oxiranes with nitrogen nucleophiles, under solid-liquid phase-transfer catalysis (SL-PTC) conditions. The β-hydroxytosyi amides resulting from the ring opening of a first epoxide with TsNH 2 was used as nucleophile, after protection of the hydroxyl group, in the reaction with a second oxirane. The morpholine skeleton has been generated through standard functional group chemistry, followed by cyclization of the intermediate p-hydroxy-β'-tosyloxy-tosylamides carried out under SL-PTC conditions. N-Tosyl Morpholines produced can be employed as building blocks in the synthesis of pharmaceuticals and as chiral tools.
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practical synthesis of enantiomerically pure Morpholines
Chimica Oggi-chemistry Today, 2008Co-Authors: Domenico Albanese, Francesca Foschi, Aaron Tagliabue, Emanuele Carlini, M PensoAbstract:Recent advances towards the synthesis of enantiomerically pure substituted Morpholines are reported.