Rhodium(I)‐Catalyzed Ene–Allene–Allene [2+2+2] Cycloadditions: Stereoselective Synthesis of Complex trans‐Fused Carbocycles

作者: Andrew T. Brusoe , Erik J. Alexanian

DOI: 10.1002/ANIE.201100272

关键词: CycloadditionAlleneEne reactionStereochemistryStereoselectivityCatalysisAlkeneRhodiumChemistry

摘要: A variety of trans-fused hydrindans and decalins is synthesized with complete stereochemistry, except for the (Z)-isomer (IV).

参考文章(67)
Sambasivarao Kotha, Enugurthi Brahmachary, Kakali Lahiri, Transition Metal Catalyzed [2+2+2] Cycloaddition and Application in Organic Synthesis European Journal of Organic Chemistry. ,vol. 2005, pp. 4741- 4767 ,(2005) , 10.1002/EJOC.200500411
Paul A. Wender, Benjamin L. Miller, Synthesis at the molecular frontier Nature. ,vol. 460, pp. 197- 201 ,(2009) , 10.1038/460197A
Robert T. Yu, Tomislav Rovis, Rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl isocyanates and alkynes. Journal of the American Chemical Society. ,vol. 128, pp. 2782- 2783 ,(2006) , 10.1021/JA057803C
Hermann A. Wegner, Armin de Meijere, Paul A. Wender, Transition metal-catalyzed intermolecular [5+2] and [5+2+1] cycloadditions of allenes and vinylcyclopropanes. Journal of the American Chemical Society. ,vol. 127, pp. 6530- 6531 ,(2005) , 10.1021/JA043671W
Corinne Aubert, Olivier Buisine, Max Malacria, The behavior of 1,n-enynes in the presence of transition metals. Chemical Reviews. ,vol. 102, pp. 813- 834 ,(2002) , 10.1021/CR980054F
Paweł Jankowski, Stanisław Marczak, Jerzy Wicha, Methods for the construction of trans-hydrindane rings and their origins in steroid chemistry. Vitamin D total synthesis Tetrahedron. ,vol. 54, pp. 12071- 12150 ,(1998) , 10.1016/S0040-4020(98)00570-5
Paul A. Wender, Vishal A. Verma, Thomas J. Paxton, Thomas H. Pillow, Function-oriented synthesis, step economy, and drug design. Accounts of Chemical Research. ,vol. 41, pp. 40- 49 ,(2008) , 10.1021/AR700155P
Marco Luparia, Laura Legnani, Alessio Porta, Giuseppe Zanoni, Lucio Toma, Giovanni Vidari, Enantioselective Synthesis and Olfactory Evaluation of Bicyclic α- and γ-Ionone Derivatives: The 3D Arrangement of Key Molecular Features Relevant to the Violet Odor of Ionones Journal of Organic Chemistry. ,vol. 74, pp. 7100- 7110 ,(2009) , 10.1021/JO9014936
Phillip T. Matsunaga, John C. Mavropoulos, Gregory L. Hillhouse, Oxygen-atom transfer from nitrous oxide (NNO) to nickel alkyls. Syntheses and reactions of nickel(II) alkoxides Polyhedron. ,vol. 14, pp. 175- 185 ,(1995) , 10.1016/0277-5387(94)00330-H