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Bin Cui - One of the best experts on this subject based on the ideXlab platform.
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preparation of trans 2 substituted 4 halopiperidines and cis 2 substituted 4 halotetrahydropyrans via alcl3 catalyzed prins reaction
Journal of Organic Chemistry, 2016Co-Authors: Gongqing Liu, Bin CuiAbstract:A general and practical method for the preparation of trans-2-substituted-4-halopiperidines and cis-2-substituted-4-halotetrahydropyrans is reported. Using 5 mol % of AlCl3 as the catalyst and 2 equiv of trimethylsilyl halides as the halide sources, aza-Prins cyclization of N-tosyl homoallylamine or Prins cyclization of Homoallylic Alcohol with carbonyl compounds could be readily realized, giving the corresponding trans-2-substituted-4-halopiperidines or cis-2-substituted-4-halotetrahydropyrans in high yields and satisfactory diastereoselectivity.
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Preparation of trans-2-Substituted-4-halopiperidines and cis-2-Substituted-4-halotetrahydropyrans via AlCl3‑Catalyzed Prins Reaction
2016Co-Authors: Gongqing Liu, Bin CuiAbstract:A general and practical method for the preparation of trans-2-substituted-4-halopiperidines and cis-2-substituted-4-halotetrahydropyrans is reported. Using 5 mol % of AlCl3 as the catalyst and 2 equiv of trimethylsilyl halides as the halide sources, aza-Prins cyclization of N-tosyl homoallylamine or Prins cyclization of Homoallylic Alcohol with carbonyl compounds could be readily realized, giving the corresponding trans-2-substituted-4-halopiperidines or cis-2-substituted-4-halotetrahydropyrans in high yields and satisfactory diastereoselectivity
Gongqing Liu - One of the best experts on this subject based on the ideXlab platform.
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preparation of trans 2 substituted 4 halopiperidines and cis 2 substituted 4 halotetrahydropyrans via alcl3 catalyzed prins reaction
Journal of Organic Chemistry, 2016Co-Authors: Gongqing Liu, Bin CuiAbstract:A general and practical method for the preparation of trans-2-substituted-4-halopiperidines and cis-2-substituted-4-halotetrahydropyrans is reported. Using 5 mol % of AlCl3 as the catalyst and 2 equiv of trimethylsilyl halides as the halide sources, aza-Prins cyclization of N-tosyl homoallylamine or Prins cyclization of Homoallylic Alcohol with carbonyl compounds could be readily realized, giving the corresponding trans-2-substituted-4-halopiperidines or cis-2-substituted-4-halotetrahydropyrans in high yields and satisfactory diastereoselectivity.
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Preparation of trans-2-Substituted-4-halopiperidines and cis-2-Substituted-4-halotetrahydropyrans via AlCl3‑Catalyzed Prins Reaction
2016Co-Authors: Gongqing Liu, Bin CuiAbstract:A general and practical method for the preparation of trans-2-substituted-4-halopiperidines and cis-2-substituted-4-halotetrahydropyrans is reported. Using 5 mol % of AlCl3 as the catalyst and 2 equiv of trimethylsilyl halides as the halide sources, aza-Prins cyclization of N-tosyl homoallylamine or Prins cyclization of Homoallylic Alcohol with carbonyl compounds could be readily realized, giving the corresponding trans-2-substituted-4-halopiperidines or cis-2-substituted-4-halotetrahydropyrans in high yields and satisfactory diastereoselectivity
Teck-peng Loh - One of the best experts on this subject based on the ideXlab platform.
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The first example of enantioselective allyl transfer from a linear Homoallylic Alcohol to an aldehyde.
Organic letters, 2002Co-Authors: Teck-peng Loh, Chi-lik Ken Lee, Kui-thong TanAbstract:The first example of enantioselective linear Homoallylic Alcohol transfer reaction was revealed. In all cases, the whole rearrangement is thermodynamically favorable and a steric effect is the driving force of this reaction. The preservation of the stereocenter and olefin geometry together with the isolation of γ-adduct Homoallylic Alcohols in one isomeric form have warranted the proposed mechanism.
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A novel method for stereoselective synthesis of β-trifluoromethylated Homoallylic Alcohols in water
Tetrahedron Letters, 1997Co-Authors: Teck-peng LohAbstract:Abstract The indium-mediated allylation reaction of aldehydes with 1,1,1-trifluoro-4-bromo-2-butene in water afforded an important trifluoromethylated building block β-trifluoromethylated Homoallylic Alcohol with high yield and excellent diastereoselectivity.
Fabien Gagosz - One of the best experts on this subject based on the ideXlab platform.
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Anti-Markovnikov Hydrofunctionalization of Alkenes
Angewandte Chemie International Edition, 2017Co-Authors: Geoffroy Hervé Lonca, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra Tejo, Fabien GagoszAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3 - or N3 -containing hypervalent iodine reagents, a series of Homoallylic Alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization of alkenols.
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anti markovnikov hydrofunctionalization of alkenes use of a benzyl group as a traceless redox active hydrogen donor
Angewandte Chemie, 2017Co-Authors: Geoffroy Hervé Lonca, Fabien Gagosz, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra TejoAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes, that utilizes a benzyl group as a traceless redox-active hydrogen donor, has been developed. Under copper catalysis and in the presence of CF3- or N3-containing hypervalent iodine reagents, a series of Homoallylic Alcohol derivatives could be regioselectivity hydrofunctionalized. A similar principle was also applied to the hydrofunctionalization of alkenols.
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Anti‐Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox‐Active Hydrogen Donor
Angewandte Chemie International Edition, 2017Co-Authors: Geoffroy Hervé Lonca, Shunsuke Chiba, Derek Yiren Ong, Thi Mai Huong Tran, Ciputra Tejo, Fabien GagoszAbstract:A protocol for the anti-Markovnikov hydrofunctionalization of alkenes, that utilizes a benzyl group as a traceless redox-active hydrogen donor, has been developed. Under copper catalysis and in the presence of CF3- or N3-containing hypervalent iodine reagents, a series of Homoallylic Alcohol derivatives could be regioselectivity hydrofunctionalized. A similar principle was also applied to the hydrofunctionalization of alkenols.
Hans-joachim Gais - One of the best experts on this subject based on the ideXlab platform.
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A Method for the Conversion of Sulfoximines to Sulfones: Application to Polymer-Bound Sulfoximines and to the Synthesis of Chiral Sulfones
European Journal of Organic Chemistry, 2000Co-Authors: Jochen Hachtel, Hans-joachim GaisAbstract:Reaction of N-alkyl, N-aryl, and N-H sulfoximines with m-chloroperbenzoic acid cleanly gives the corresponding sulfones in high yield. In the case of the cleavage of N-alkyl and N-arylsulfoximines, formation of the corresponding nitroso compounds as the other reaction product was proven. Starting from enantio- and diastereopure sulfoximines, a number of chiral sulfones, including the axially chiral sulfone 6 and the sulfonyl-functionalized Homoallylic Alcohol 8, have been prepared. Reaction of the enantiopure sulfoximine 30 with Merrifield resin gave the polymer-bound sulfoximine 32. Oxidative cleavage of 32 afforded the sulfone 16 in high yield. Deprotonation of the sulfoximine resin 32 and reaction of Li-32 with benzaldehyde and propanal furnished the β-hydroxysulfoximine resins 33a and 33b, respectively. Oxidative cleavage of 33a and 33b readily afforded the β-hydroxy sulfones 14a and 14b, respectively.
