참고문헌 (55)

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2. For a general review see: 

3. Pandey, G., Banerjee, P., Gadre, S. R.. Construction of Enantiopure Pyrrolidine Ring System via Asymmetric [3+2]-Cycloaddition of Azomethine Ylides. Chemical reviews, vol.106, no.11, 4484-4517.

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4. Stanley, Levi M., Sibi, Mukund P.. Enantioselective Copper-Catalyzed 1,3-Dipolar Cycloadditions. Chemical reviews, vol.108, no.8, 2887-2902.

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5. Husinec, Suren, Savic, Vladimir. Chiral catalysts in the stereoselective synthesis of pyrrolidine derivatives via metallo-azomethine ylides. Tetrahedron, asymmetry, vol.16, no.12, 2047-2061.

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6. Kissane, Marie, Maguire, Anita R.. Asymmetric 1,3-dipolar cycloadditions of acrylamides. Chemical Society reviews, vol.39, no.2, 845-883.

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7. Yeom, Hyun-Suk, Lee, Ji-Eun, Shin, Seunghoon. Gold-Catalyzed Waste-Free Generation and Reaction of Azomethine Ylides: Internal Redox/Dipolar Cycloaddition Cascade. Angewandte Chemie, vol.120, no.37, 7148-7151.

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8. Yeom, Hyun-Suk, Lee, Ji-Eun, Shin, Seunghoon. Gold-Catalyzed Waste-Free Generation and Reaction of Azomethine Ylides: Internal Redox/Dipolar Cycloaddition Cascade. Angewandte Chemie. international edition, vol.47, no.37, 7040-7043.

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9. Yeom, Hyun-Suk, Lee, Youngun, Lee, Ji-Eun, Shin, Seunghoon. Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles. Organic & biomolecular chemistry, vol.7, no.22, 4744-4752.

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10. Yeom, Hyun-Suk, Lee, Youngun, Jeong, Jaewon, So, Eunsoo, Hwang, Soojin, Lee, Ji-Eun, Lee, Shim Sung, Shin, Seunghoon. Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6-Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade. Angewandte Chemie, vol.122, no.9, 1655-1658.

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11. Yeom, Hyun-Suk, Lee, Youngun, Jeong, Jaewon, So, Eunsoo, Hwang, Soojin, Lee, Ji-Eun, Lee, Shim Sung, Shin, Seunghoon. Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6-Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade. Angewandte Chemie. international edition, vol.49, no.9, 1611-1614.

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12. Cui, Li, Zhang, Guozhu, Peng, Yu, Zhang, Liming. Gold or No Gold: One-Pot Synthesis of Tetrahydrobenz[b]azepin-4-ones from Tertiary N-(But-3-ynyl)anilines. Organic letters, vol.11, no.6, 1225-1228.

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13. Cui, Li, Peng, Yu, Zhang, Liming. A Two-Step, Formal [4 + 2] Approach toward Piperidin-4-ones via Au Catalysis. Journal of the American Chemical Society, vol.131, no.24, 8394-8395.

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14. Ye, Longwu, Cui, Li, Zhang, Guozhu, Zhang, Liming. Alkynes as Equivalents of α-Diazo Ketones in Generating α-Oxo Metal Carbenes: A Gold-Catalyzed Expedient Synthesis of Dihydrofuran-3-ones. Journal of the American Chemical Society, vol.132, no.10, 3258-3259.

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15. Shapiro, N. D., Toste, F. D.. Rearrangement of Alkynyl Sulfoxides Catalyzed by Gold(I) Complexes. Journal of the American Chemical Society, vol.129, no.14, 4160-4161.

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16. Li, Guotao, Zhang, Liming. Gold-Catalyzed Intramolecular Redox Reaction of Sulfinyl Alkynes: Efficient Generation of α-Oxo Gold Carbenoids and Application in Insertion into R&n.bond;CO Bonds. Angewandte Chemie, vol.119, no.27, 5248-5251.

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17. Li, Guotao, Zhang, Liming. Gold-Catalyzed Intramolecular Redox Reaction of Sulfinyl Alkynes: Efficient Generation of α-Oxo Gold Carbenoids and Application in Insertion into R&n.bond;CO Bonds. Angewandte Chemie. international edition, vol.46, no.27, 5156-5159.

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18. Davies, Paul W., Albrecht, Sébastien J.‐C.. Gold‐ or Platinum‐Catalyzed Synthesis of Sulfur Heterocycles: Access to Sulfur Ylides without Using Sacrificial Functionality. Angewandte Chemie, vol.121, no.44, 8522-8525.

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19. Davies, Paul W., Albrecht, Sébastien J.‐C.. Gold‐ or Platinum‐Catalyzed Synthesis of Sulfur Heterocycles: Access to Sulfur Ylides without Using Sacrificial Functionality. Angewandte Chemie. international edition, vol.48, no.44, 8372-8375.

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20. Li, Chia‐Wen, Pati, Kamalkishore, Lin, Guan‐You, Sohel, Shariar Md. Abu, Hung, Hsiao‐Hua, Liu, Rai‐Shung. Gold‐Catalyzed Oxidative Ring Expansions and Ring Cleavages of Alkynylcyclopropanes by Intermolecular Reactions Oxidized by Diphenylsulfoxide. Angewandte Chemie, vol.122, no.51, 10087-10090.

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21. Li, Chia‐Wen, Pati, Kamalkishore, Lin, Guan‐You, Sohel, Shariar Md. Abu, Hung, Hsiao‐Hua, Liu, Rai‐Shung. Gold‐Catalyzed Oxidative Ring Expansions and Ring Cleavages of Alkynylcyclopropanes by Intermolecular Reactions Oxidized by Diphenylsulfoxide. Angewandte Chemie. international edition, vol.49, no.51, 9891-9894.

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22. For reviews on 3‐oxidopyridinium salt see: 

23. Katritzky, Alan R., Dennis, Nicholas. Cycloaddition reactions of heteroaromatic six-membered rings. Chemical reviews, vol.89, no.4, 827-861.

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24. Peese, Kevin M., Gin, David Y.. Asymmetric Synthetic Access to the Hetisine Alkaloids: Total Synthesis of (+)-Nominine. Chemistry : a European journal, vol.14, no.5, 1654-1665.

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25. For acyclic α‐methylbenzyl amine derivatives asN‐modified chiral auxiliaries in intermolecular [3+2] cycloaddition reactions see: 

26. Padwa, A., Chen, Y.-Y., Chiacchio, U., Dent, W.. Diastereofacial selectivity in azomethine ylide cycloaddition reactions derived from chiral α-cyanoaminosilanes. Tetrahedron, vol.41, no.17, 3529-3535.

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27. Rouden, J., Royer, J., Husson, H.-P.. Asymmetric synthesis XVII : Facile generation of a chiral azomethine ylide via the CN(R,S) method. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.30, no.38, 5133-5136.

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28. Deprez, P., Royer, J., Husson, H.-P.. High diastereofacial selectivity in the 1,3-dipolar cycloaddition of chiral azomethine ylides. Tetrahedron, asymmetry, vol.2, no.12, 1189-1192.

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29. Garner, Philip, Ho, Wen Bin, Grandhee, Sunitha K., Youngs, Wiley J., Kennedy, Vance O.. Development of an asymmetric approach to the 3,8-diazabicyclo[3.2.1]octane moiety of quinocarcin via intramolecular 1,3-dipolar cycloadditions of photochemically generated azomethine ylides. Journal of organic chemistry, vol.56, no.20, 5893-5903.

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30. Williams, Robert M., Zhai, Weixu, Aldous, David J., Aldous, Suzanne C.. Asymmetric [1,3]-dipolar cycloaddition reactions: synthesis of highly substituted proline derivatives. Journal of organic chemistry, vol.57, no.24, 6527-6532.

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31. Garner, Philip, Sunitha, Krishnan, Ho, Wen Bin, Youngs, Wiley J., Kennedy, Vance O., Djebli, Abdellah. An asymmetric approach to naphthyridinomycin and quinocarcin via a remarkably selective intramolecular 1,3-dipolar cycloaddition reaction. Journal of organic chemistry, vol.54, no.9, 2041-2042.

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32. Jones, Raymond C.F., Howard, Kevin J, Snaith, John S. A rapid assembly of homochiral 2,3,4-trisubstituted pyrrolidines. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.38, no.9, 1647-1650.

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33. Harwood, L.M., Lilley, I.A.. Enantiocontrolled construction of bicyclic proline derivatives via one-pot generation and intramolecular trapping of chiral stabilised azomethine ylids. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.34, no.3, 537-540.

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34. Drew, Michael G.B., Harwood, Laurence M., Price, David W., Choi, M.-S., Park, Gyoosoon. Computational studies on the asymmetric induction in intramolecular 1,3-dipolar cycloaddition of (S)-5-phenyl-morpholin-2-one. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.41, no.26, 5077-5081.

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35. Our initial efforts to use AuI‐ or AuIIIcomplexes with chiral ligands (including binap quinap and Segphos‐derivatives) led to a virtually racemic mixture of products or little conversion if any presumably owing to a premature turnover of the catalyst fromD(Scheme 1 b). The reactions with AuIcomplexes were also accompanied by the formation of isoindole side‐products (Ref. [3 a] and [3 b]). 

36. Asymmetric activation of alkynes with a AuIII‐complex has not been reported to our knowledge. For recent reviews on asymmetric gold‐catalyzed transformations see: 

37. Widenhoefer, Ross A.. Recent Developments in Enantioselective Gold(I) Catalysis. Chemistry : a European journal, vol.14, no.18, 5382-5391.

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38. Sengupta, Sujata, Shi, Xiaodong. Recent Advances in Asymmetric Gold Catalysis. ChemCatChem, vol.2, no.6, 609-619.

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39. Ishida, Kento, Kusama, Hiroyuki, Iwasawa, Nobuharu. Enantioselective Preparation of 8-Oxabicyclo[3.2.1]octane Derivatives via Asymmetric [3+2]-Cycloaddition of Platinum-Containing Carbonyl Ylides with Vinyl Ethers. Journal of the American Chemical Society, vol.132, no.26, 8842-8843.

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40. Tokuyama, H., Kuboyama, T., Amano, A., Yamashita, T., Fukuyama, T.. A Novel Transformation of Primary Amines to N-Monoalkylhydroxylamines. Synthesis : journal of synthetic organic chemistry, vol.2000, no.9, 1299-1304.

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41. 10.15227/orgsyn.080.0207 

    

42. Bode, Jeffrey W., Fox, Ryan M., Baucom, Kyle D.. Chemoselective Amide Ligations by Decarboxylative Condensations of N-Alkylhydroxylamines and α-Ketoacids. Angewandte Chemie, vol.118, no.8, 1270-1274.

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43. Bode, Jeffrey W., Fox, Ryan M., Baucom, Kyle D.. Chemoselective Amide Ligations by Decarboxylative Condensations of N-Alkylhydroxylamines and α-Ketoacids. Angewandte Chemie. international edition, vol.45, no.8, 1248-1252.

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44. Assignment of the absolute stereochemistry of1iis based on the X‐ray crystallography on2i(Figure 2 see the Supporting Information for details of the X‐ray crystallographic procedure). Repeated recrystallization (x5) increased the enantioselectivity of (S)‐(−)‐1ito>99 %ee. 

45. In cases where lower yields were obtained the reaction was accompanied by unidentified decomposition products (observed in the crude1H NMR spectrum) possibly owing to the regio‐isomeric redox process (e.g. to form isoindole and/or its decomposition by‐products: see Ref. [3 b]). However these side‐products were not the corresponding diastereomers as indicated by the absence of the characteristic AB quartet pattern and the presence of messy olefinic resonances in the crude1H NMR spectrum. The desired isomer3was cleanly separated by column chromatography on silica gel in the indicated yields. 

46. For the analogous polar effect in carbonyl additions see: 

47. Cherest, M., Felkin, H., Prudent, N.. Torsional strain involving partial bonds. The stereochemistry of the lithium aluminium hydride reduction of some simple open-chain ketones. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.9, no.18, 2199-2204.

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48. Nouv. J. Chim. Anh N. T. 61 1 1977 

49. Becke, Axel D.. Density-functional thermochemistry. III. The role of exact exchange. The Journal of chemical physics, vol.98, no.7, 5648-5652.

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50. A Chemist’s Guide to Density Functional Theory Koch W. 2000 

51. Density Functional Theory of Atoms and Molecules Parr R. G. 1989 

52. Gaussian 03 Revision D.02 M. J. Frisch et al. Gaussian Inc. Pittsburgh PA 2004(Full reference given in the Supporting Information).