Construction of Azabicyclo[6.4.0]dodecatrienes Based on Rhodium(I)-Catalyzed Intramolecular [6+2] Cycloaddition between Azetidine, Allene, and Alkynes
Authors:
Open Access
- 1 January 2016
- journal article
- research article
- Published by Pharmaceutical Society of Japan in Chemical and Pharmaceutical Bulletin
- Vol. 64 (7) , 805-810
Abstract
Treatment of the allenylazetidine-alkynes with a catalytic amount of [RhCl(CO)dppp]2 (dppp: 1,3-bis(diphenylphosphino)propane) effected the intramolecular hetero-[6+2]-type ring-closing reaction via the C-C bond cleavage of the azetidine ring to produce azabicyclo[6.4.0]dodecatriene derivatives in good to excellent yields. The formation of the oxa analogue could also be achieved.Keywords
This publication has 21 references indexed in Scilit:
- Catalytic C–C Bond Activations via Oxidative Addition to Transition MetalsChemical Reviews, 2015
- Rhodium(I)‐Catalyzed Cycloisomerization of Alkene‐Substituted Allenylcyclopropanes: Stereoselective Formation of Bicyclo[4.3.0]nonadienesAngewandte Chemie International Edition, 2013
- Csp3–Csp3 and Csp3–H Bond Activation of 1,1-Disubstituted CyclopentaneJournal of the American Chemical Society, 2012
- Transition‐Metal‐Mediated Cleavage and Activation of C–C Single BondsEuropean Journal of Organic Chemistry, 2012
- Transition-Metal-Catalyzed Rearrangements of Small Cycloalkanes: Regioselectivity Trends in β-Carbon Elimination ReactionsSynthesis, 2011
- RhI‐Catalyzed [6+2] Cycloaddition of Alkyne–Allenylcyclobutanes: A New Entry for the Synthesis of Bicyclo[6.m.0] SkeletonsChemistry – A European Journal, 2011
- Metal-catalysed cleavage of carbon–carbon bondsChemical Communications, 2010
- Rhodium(I)‐Catalyzed Intramolecular [5+2] Cycloaddition Reactions of Alkynes and Allenylcyclopropanes: Construction of Bicyclo[5.4.0]undecatrienes and Bicyclo[5.5.0]dodecatrienesAngewandte Chemie International Edition, 2010
- Enantioselective metal-catalyzed activation of strained ringsOrganic & Biomolecular Chemistry, 2009
- Heats of combustion and formation of cyclopropaneJournal of Research of the National Bureau of Standards, 1949