참고문헌 (72)

1. For a recent review of cycloaddition and cycloisomerization reactions see:Comprehensive Organic Synthesis II Vol. 5(Eds.: P. Knochel G. A. Molander A. Fürstner) Elsevier: Waltham 2014. 

2. For recent reviews on metal-catalyzed higher-order carbocyclization reactions see: 

3. Inglesby, Phillip A., Evans, P. Andrew. Stereoselective transition metal-catalysed higher-order carbocyclisation reactions. Chemical Society reviews, vol.39, no.8, 2791-2805.

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4. Gulías, Moisés, López, Fernando, Mascareñas, José L.. Development of transition-metal-catalyzed cycloaddition reactions leading to polycarbocyclic systems. Pure and applied chemistry. : Chimie pure et appliqueé, vol.83, no.3, 495-506.

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5. Science of Synthesis, Vol. 3 Aubert C. 145 2011 

6. Broere, Daniël L. J., Ruijter, Eelco. Recent Advances in Transition-Metal-Catalyzed [2+2+2]-Cyclo(co)trimerization Reactions. Synthesis : journal of synthetic organic chemistry, vol.44, no.17, 2639-2672.

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7. 10.1016/B978-0-08-097742-3.00515-2 

   

8. Lam, Heather, Lautens, Mark. Recent Advances in Transition-Metal-Catalyzed (4+3)-Cycloadditions. Synthesis : journal of synthetic organic chemistry, vol.52, no.17, 2427-2449.

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9. For seminal examples of the metal-catalyzed cyclotrimerization of acetylene and propargyl alcohol see: 

10. Cyclisierende Polymerisation von Acetylen. III Benzol, Benzolderivate und hydroaromatische Verbindungen. Justus Liebigs Annalen der Chemie, vol.560, no.1, 104-116.

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11. Seances Acad. Sci. Berthelot M. 905 62 1866 

12. For reviews on the construction of carbocyclic seven-membered rings and their application to total synthesis see: 

13. Battiste, Merle A., Pelphrey, Phillip M., Wright, Dennis L.. The Cycloaddition Strategy for the Synthesis of Natural Products Containing Carbocyclic Seven-Membered Rings. Chemistry : a European journal, vol.12, no.13, 3438-3447.

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14. Arnold, Jeffrey S., Nguyen, Hien M.. Rhodium-Catalyzed Asymmetric Amination of Allylic Trichloroacetimidates. Synthesis : journal of synthetic organic chemistry, vol.45, no.15, 2101-2108.

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15. Trost, Barry M., Zuo, Zhijun, Schultz, Johnathan E.. Transition‐Metal‐Catalyzed Cycloaddition Reactions to Access Seven‐Membered Rings. Chemistry : a European journal, vol.26, no.67, 15354-15377.

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16. For our selected studies on the formation of seven-membered rings see: 

17. Evans, P. Andrew, Inglesby, Phillip A.. Intermolecular Rhodium-Catalyzed [3+2+2] Carbocyclization of Alkenylidenecyclopropanes with Activated Alkynes: Regio- and Diastereoselective Construction of cis-Fused Bicycloheptadienes. Journal of the American Chemical Society, vol.130, no.39, 12838-12839.

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18. Evans, P.A., Baikstis, T., Inglesby, P.A.. Stereoselective rhodium-catalyzed [(3+2)+2] carbocyclization reaction of trialkoxysilyl-substituted alkenylidenecyclopropanes with monosubstituted alkynes. Tetrahedron, vol.69, no.36, 7826-7830.

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19. For selected examples of [3+2+2] carbocyclization reactions mediated by stoichiometric metal complexes see: 

20. Barluenga, J., Vicente, R., Barrio, P., Lopez, L. A., Tomas, M., Borge, J.. Specific Synthesis of 1,2- and 1,3-Dialkylidenecycloheptanes by [3+2+2] Cyclization of Alkenyl Fischer Carbene Complexes and Allenes. Journal of the American Chemical Society, vol.126, no.44, 14354-14355.

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21. Older, C. M., McDonald, R., Stryker, J. M.. Unprecedented Coordination Modes and Demetalation Pathways for Unbridged Polyenyl Ligands. Ruthenium &eegr;¹,&eegr;⁴-Cycloheptadienyl Complexes from Allyl/Alkyne Cycloaddition. Journal of the American Chemical Society, vol.127, no.41, 14202-14203.

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22. For examples of intermolecular metal-catalyzed [3+2+2] reactions see: 

23. Saito, S., Masuda, M., Komagawa, S.. Nickel-Catalyzed Intermolecular [3 + 2 + 2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes. Journal of the American Chemical Society, vol.126, no.34, 10540-10541.

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24. Komagawa, Shinsuke, Saito, Shinichi. Nickel-Catalyzed Three-Component [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes—Selective Synthesis of Multisubstituted Cycloheptadienes. Angewandte Chemie. international edition, vol.45, no.15, 2446-2449.

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25. Zhao, Wanxiang, Zhang, Junliang. Rhodium-catalyzed domino heterocyclization and [(3+2)+2] carbocyclization: construction of fused tricycloheptadienes. Chemical communications : Chem comm, vol.46, no.41, 7816-7818.

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26. Saya, Lucía, Bhargava, Gaurav, Navarro, Miguel A., Gulías, Moises, López, Fernando, Fernández, Israel, Castedo, Luis, Mascareñas, José L.. Nickel‐Catalyzed [3+2+2] Cycloadditions between Alkynylidenecyclopropanes and Activated Alkenes. Angewandte Chemie. international edition, vol.49, no.51, 9886-9890.

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27. Saya, Lucía, Fernández, Israel, López, Fernando, Mascareñas, José L.. Nickel-Catalyzed Intramolecular [3 + 2 + 2] Cycloadditions of Alkylidenecyclopropanes. A Straightforward Entry to Fused 6,7,5-Tricyclic Systems. Organic letters, vol.16, no.19, 5008-5011.

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28. Evans, P. Andrew, Negru, Daniela E., Shang, Deju. Rhodium‐Catalyzed [(3+2)+2] Carbocyclization of Alkynylidenecyclopropanes with Substituted Allenes: Stereoselective Construction of Tri‐ and Tetrasubstituted Exocyclic Olefins. Angewandte Chemie. international edition, vol.54, no.16, 4768-4772.

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29. Evans, P. Andrew, Inglesby, Phillip A., Kilbride, Kathryn. A Concise Total Synthesis of Pyrovellerolactone Using a Rhodium-Catalyzed [(3 + 2) + 2] Carbocyclization Reaction. Organic letters, vol.15, no.8, 1798-1801.

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30. For examples of intramolecular metal-catalyzed [3+2+2] reactions see: 

31. Bhargava, Gaurav, Trillo, Beatriz, Araya, Marisel, López, Fernando, Castedo, Luis, Mascareñas, José L.. Palladium-catalyzed [3C + 2C + 2C] cycloaddition of enynylidenecyclopropanes: efficient construction of fused 5-7-5 tricyclic systems. Chemical communications : Chem comm, vol.46, no.2, 270-272.

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32. Araya, Marisel, Gulías, Moisés, Fernández, Israel, Bhargava, Gaurav, Castedo, Luis, Mascareñas, José Luis, López, Fernando. Rhodium‐Catalyzed Intramolecular [3+2+2] Cycloadditions between Alkylidenecyclopropanes, Alkynes, and Alkenes. Chemistry : a European journal, vol.20, no.33, 10255-10259.

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33. For examples of tremulane sesquiterpene natural products containing lactone rings see: 

34. Ayer, William A., Cruz, Elizabete R.. The tremulanes, a new group of sesquiterpenes from the aspen rotting fungus Phellinus tremulae. Journal of organic chemistry, vol.58, no.26, 7529-7534.

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35. Liu, Dong-Ze., Wang, Fei., Liu, Ji-Kai.. Sesquiterpenes from Cultures of the Basidiomycete Conocybe siliginea. Journal of natural products, vol.70, no.9, 1503-1506.

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36. Zhou, Zhong-Yu, Tang, Jian-Guo, Wang, Fei, Dong, Ze-Jun, Liu, Ji-Kai. Sesquiterpenes and Aliphatic Diketones from Cultures of the Basidiomycete Conocybe siliginea. Journal of natural products, vol.71, no.8, 1423-1426.

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37. Wu, Xiuli, Lin, Sheng, Zhu, Chenggen, Yue, Zhenggang, Yu, Yang, Zhao, Feng, Liu, Bo, Dai, Jungui, Shi, Jiangong. Homo- and Heptanor-sterols and Tremulane Sesquiterpenes from Cultures of Phellinus igniarius. Journal of natural products, vol.73, no.7, 1294-1300.

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38. Ying, Y.M., Shan, W.G., Zhang, L.W., Zhan, Z.J.. Ceriponols A-K, tremulane sesquitepenes from Ceriporia lacerate HS-ZJUT-C13A, a fungal endophyte of Huperzia serrata. Phytochemistry, vol.95, 360-367.

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39. CCDC-1988836 contains supplementary crystallographic data forbis-bromocarbamate4. This data can be obtained free of charge from Cambridge Crystallographic Data Centre (CCDC)viawww.ccdc.cam.ac.uk/data request/cif. X-ray analysis of4confirmed thecis-configuration of the hydrogen atoms at the rings fusions. 

40. For computational studies on the activation of ACPs and an example of the isolation and characterization of the Rh-TMM complex see: 

41. Mazumder, Shivnath, Shang, Deju, Negru, Daniela E., Baik, Mu-Hyun, Evans, P. Andrew. Stereoselective Rhodium-Catalyzed [3 + 2 + 1] Carbocyclization of Alkenylidenecyclopropanes with Carbon Monoxide: Theoretical Evidence for a Trimethylenemethane Metallacycle Intermediate. Journal of the American Chemical Society, vol.134, no.51, 20569-20572.

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42. Inglesby, Phillip A., Bacsa, John, Negru, Daniela E., Evans, P. Andrew. The Isolation and Characterization of a Rhodacycle Intermediate Implicated in Metal‐Catalyzed Reactions of Alkylidenecyclopropanes. Angewandte Chemie. international edition, vol.53, no.15, 3952-3956.

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43. For an example of interpretation on impact of Pitzer strains to selectivities of organic synthesis see: 

44. Pitzer, Kenneth S., Donath, Wilm E.. Conformations and Strain Energy of Cyclopentane and its Derivatives. Journal of the American Chemical Society, vol.81, no.13, 3213-3218.

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45. Cremer, Dieter., Gauss, Juergen.. Theoretical determination of molecular structure and conformation. 20. Reevaluation of the strain energies of cyclopropane and cyclobutane carbon-carbon and carbon-hydrogen bond energies, 1,3 interactions, and .sigma.-aromaticity. Journal of the American Chemical Society, vol.108, no.24, 7467-7477.

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46. Cruz, Elizabete R.. The biosynthesis of the new tremulane sesquiterpenes isolated from Phellinus tremulae. Canadian journal of chemistry, vol.75, no.6, 834-839.

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47. Davies, H. M. L., Doan, B. D.. Total Synthesis of (±)-Tremulenolide A and (±)-Tremulenediol A via a Stereoselective Cyclopropanation/Cope Rearrangement Annulation Strategy. Journal of organic chemistry, vol.63, no.3, 657-660.

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48. Davies, H. M. L., Doan, B. D.. Enantioselective Synthesis of Fused Cycloheptadienes by a Tandem Intramolecular Cyclopropanation/Cope Rearrangement Sequence. Journal of organic chemistry, vol.64, no.23, 8501-8508.

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49. Ashfeld, B. L., Martin, S. F.. Enantioselective Syntheses of Tremulenediol A and Tremulenolide A. Organic letters, vol.7, no.20, 4535-4537.

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50. Ashfeld, Brandon L., Martin, Stephen F.. Enantioselective syntheses of tremulenediol A and tremulenolide A. Tetrahedron, vol.62, no.45, 10497-10506.

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51. For reviews on substrate-directed reactions see: 

52. Hoveyda, Amir H., Evans, David A., Fu, Gregory C.. Substrate-directable chemical reactions. Chemical reviews, vol.93, no.4, 1307-1370.

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53. 10.1002/(SICI)1521-3765(20000502)6:9<1519::AID-CHEM1519>3.0.CO;2-6 

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54. Eisenbraun, E. J., George, Thomas, Riniker, B., Djerassi, Carl. Terpenoids. XLIII.¹ On the Absolute Configuration on Guaiol. Correlation with Nepetalinic Acid². Journal of the American Chemical Society, vol.82, no.14, 3648-3652.

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55. Brown, John M., Naik, Ramachandra G.. Chelate control in the rhodium-catalysed homogeneous hydrogenation of chiral allylic and homoallylic alcohols. Journal of the Chemical Society, Chemical communications, vol.1982, no.6, 348-350.

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56. Stork, Gilbert, Kahne, Daniel E.. Stereocontrol in homogeneous catalytic hydrogenation via hydroxyl group coordination. Journal of the American Chemical Society, vol.105, no.4, 1072-1073.

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57. Crabtree, Robert H., Davis, Mark W.. Occurrence and origin of a pronounced directing effect of a hydroxyl group in hydrogenation with [Ir(cod)P(C6H11)3(py)]PF6. Organometallics, vol.2, no.5, 681-682.

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58. For examples of a similar base mediated epimerization see: 

59. House, Herbert O., Gaa, Peter C., Lee, Joseph H. C., VanDerveer, Don. Perhydroazulenes. 4. 6-tert-Butyl-4-oxoperhydroazulene system. Journal of organic chemistry, vol.48, no.10, 1670-1678.

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60. Sworin, Michael, Lin, Ko Chung. An oxy-Cope approach to hydroazulenoids. Synthetic and mechanistic aspects of thermal cyclization reactions. Journal of the American Chemical Society, vol.111, no.5, 1815-1825.

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61. Science of Synthesis Brandsma L. 285 8 2006 

62. Hay, P. Jeffrey, Wadt, Willard R.. Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg. The Journal of chemical physics, vol.82, no.1, 270-283.

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63. Becke, A. D.. Density-functional exchange-energy approximation with correct asymptotic behavior. Physical review. A, General physics, vol.38, no.6, 3098-3100.

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64. Lee, Chengteh, Yang, Weitao, Parr, Robert G.. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical review. B, Condensed matter, vol.37, no.2, 785-789.

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65. Dunning Jr., Thom H.. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen. The Journal of chemical physics, vol.90, no.2, 1007-1023.

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66. Marten, B., Kim, K., Cortis, C., Friesner, R. A., Murphy, R. B., Ringnalda, M. N., Sitkoff, D., Honig, B.. New Model for Calculation of Solvation Free Energies: Correction of Self-Consistent Reaction Field Continuum Dielectric Theory for Short-Range Hydrogen-Bonding Effects. The Journal of physical chemistry, vol.100, no.28, 11775-11788.

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67. Grimme, Stefan, Antony, Jens, Ehrlich, Stephan, Krieg, Helge. A consistent and accurateab initioparametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. The Journal of chemical physics, vol.132, no.15, 154104-.

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68. Bochevarov, Art D., Harder, Edward, Hughes, Thomas F., Greenwood, Jeremy R., Braden, Dale A., Philipp, Dean M., Rinaldo, David, Halls, Mathew D., Zhang, Jing, Friesner, Richard A.. Jaguar: A high‐performance quantum chemistry software program with strengths in life and materials sciences. International journal of quantum chemistry, vol.113, no.18, 2110-2142.

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