Modular mesoionics: understanding and controlling regioselectivity in 1,3-dipolar cycloadditions of Münchnone derivatives.

作者: Marie S. T. Morin , Daniel J. St-Cyr , Bruce A. Arndtsen , Elizabeth H. Krenske , K. N. Houk

DOI: 10.1021/JA406833Q

关键词:

摘要: 1,3-Dipolar cycloadditions of mesoionic 1,3-dipoles (Münchnones, imino-Münchnones, and phospha-Münchnones) with alkynes offer versatile, modular synthetic routes to pyrroles…

参考文章(50)
Bruce D. Roth, C. J. Blankley, A. W. Chucholowski, E. Ferguson, M. L. Hoefle, D. F. Ortwine, R. S. Newton, C. S. Sekerke, D. R. Sliskovic, M Wilson, Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran 2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus Journal of Medicinal Chemistry. ,vol. 34, pp. 357- 366 ,(1991) , 10.1021/JM00105A056
Mark T. Bilodeau, April M. Cunningham, SOLID-SUPPORTED SYNTHESIS OF IMIDAZOLES : A STRATEGY FOR DIRECT RESIN-ATTACHMENT TO THE IMIDAZOLE CORE Journal of Organic Chemistry. ,vol. 63, pp. 2800- 2801 ,(1998) , 10.1021/JO980027P
Daniel H. Ess, K. N. Houk, Theory of 1,3-Dipolar Cycloadditions: Distortion/Interaction and Frontier Molecular Orbital Models Journal of the American Chemical Society. ,vol. 130, pp. 10187- 10198 ,(2008) , 10.1021/JA800009Z
Piero Dalla Croce, Raffaella Ferraccioli, Concetta La Rosa, Reaction of mesoionic compounds deriving from cyclic N-acyl-α-aminoacids with N-(phenylmethylene)benzenesulfonamide Tetrahedron. ,vol. 55, pp. 201- 210 ,(1999) , 10.1016/S0040-4020(98)01026-6
Axel D. Becke, A New Mixing of Hartree-Fock and Local Density-Functional Theories Journal of Chemical Physics. ,vol. 98, pp. 1372- 1377 ,(1993) , 10.1063/1.464304
Ronald A. Eade, J. Campbell Earl, 118. The sydnones. A new class of compound containing two adjacent nitrogen atoms Journal of the Chemical Society (Resumed). pp. 591- 593 ,(1946) , 10.1039/JR9460000591