Heterocumulenes as 2π partners in metal-promoted [6π+2π] cycloaddition reactions

作者: James H. Rigby , Gulzar Ahmed , Mark D. Ferguson

DOI: 10.1016/S0040-4039(00)73918-9

关键词: ChromiumMetalHeterocumuleneOrganic chemistryChemistryMedicinal chemistryAlkylArylCycloadditionBiochemistryDrug discovery

摘要: Abstract Alkyl and aryl substituted isocyanates ketenes have been shown to be useful 2π partners in photoinitiated chromium(O)-promoted [6π+2π] cycloaddition reactions.

参考文章(20)
James H. Rigby, N. Balasubramanian, Preparation of highly substituted 2-pyridones by reaction of vinyl isocyanates and enamines Journal of Organic Chemistry. ,vol. 54, pp. 224- 228 ,(1989) , 10.1021/JO00262A047
Ken S. Feldman, Jon H. Come, Alan J. Freyer, Ben J. Kosmider, Cynthia M. Smith, Synthesis of eight-membered carbocycles via intramolecular [6π+2π] photocycloaddition of alkenyltropones Journal of the American Chemical Society. ,vol. 108, pp. 1327- 1328 ,(1986) , 10.1021/JA00266A050
Rowland Pettit, John Stanley Ward, Cycloaddition reactions between cyclobutadiene and unsaturated molecules coordinated to iron Journal of the American Chemical Society. ,vol. 93, pp. 262- 264 ,(1971) , 10.1021/JA00730A051
Ken S. Feldman, Jon H. Come, Benedict J. Kosmider, Pamela M. Smith, David P. Rotella, Ming Jung Wu, Mechanistic and preparative studies of the intramolecular photocyclization of methylated 2-(4-pentenyl)tropones Journal of Organic Chemistry. ,vol. 54, pp. 592- 601 ,(1989) , 10.1021/JO00264A017
Karen Chaffee, John B. Sheridan, Arnis Aistars, Photoinduced [6 + 2] cycloadditions of alkynes to tricarbonylcycloheptatrienechromium(0) Organometallics. ,vol. 11, pp. 18- 19 ,(1992) , 10.1021/OM00037A010
James H. Rigby, Vincent P. Sandanayaka, Intramolecular chromium(0) promoted higher-order cycloaddition reactions Tetrahedron Letters. ,vol. 34, pp. 935- 938 ,(1993) , 10.1016/S0040-4039(00)77458-2
James H. Rigby, Humy S. Ateeq, Nelly R. Charles, Stephane V. Cuisiat, Mark D. Ferguson, James A. Henshilwood, A. Chris Krueger, Cyprian O. Ogbu, Kevin M. Short, M. J. Heeg, Metal-promoted higher-order cycloaddition reactions. Stereochemical, regiochemical, and mechanistic aspects of the [6.pi. + 4.pi.] reaction Journal of the American Chemical Society. ,vol. 115, pp. 1382- 1396 ,(1993) , 10.1021/JA00057A023
James H. Rigby, Humy S. Ateeq, A. Chris Krueger, Metal promoted higher-order cycloaddition reactions. A facile entry into substituted eight- and ten-membered carbocycles. Tetrahedron Letters. ,vol. 33, pp. 5873- 5876 ,(1992) , 10.1016/S0040-4039(00)61076-6
Ingrid Fischler, Friedrich-Wilhelm Grevels, Johannes Leitich, Saim Özkar, Photoinduced Reactions of Cr(CO)3‐Coordinated 1,3,5‐Cycloheptatriene: [6 + 2] Cycloaddition with an Alkyne and Catalytic 1,6‐Hydrogenation Chemische Berichte. ,vol. 124, pp. 2857- 2861 ,(1991) , 10.1002/CBER.19911241229