Selective hydrogenation of indolizines: an expeditious approach to derive tetrahydroindolizines and indolizidines from morita-baylis-hillman adducts.
作者： Bruno V. M. Teodoro , José Tiago M. Correia , Fernando Coelho
DOI: 10.1021/JO502471Q
关键词:
摘要: In this study, we describe the hydrogenation of indolizines derived from Morita–Baylis–Hillman adducts. We demonstrate that functionalized tetrahydroindolizines and indolizidines can be prepared selectively, at low pressure, by simply adjusting acidity medium. Using simple straightforward strategy, substituted were obtained diastereoselectively in high yield.
acs.org
fapesp.br
sci-hub.se 参考文章(68)
F.J. Swinbourne, J.H. Hunt, G. Klinkert, Advances in Indolizine Chemistry ChemInform. ,vol. 23, pp. 103- 170 ,(1979) , 10.1016/S0065-2725(08)60842-9
Mercedes Alonso, Paul Geerlings, Frank De Proft, Topology switching in [32]heptaphyrins controlled by solvent, protonation, and meso substituents. Chemistry: A European Journal. ,vol. 19, pp. 1617- 1628 ,(2013) , 10.1002/CHEM.201203295
Alexandru V. Rotaru, Ioan D. Druta, Thomas Oeser, Thomas J. J. Müller, A Novel Coupling 1,3-Dipolar Cycloaddition Sequence as a Three-Component Approach to Highly Fluorescent Indolizines Helvetica Chimica Acta. ,vol. 88, pp. 1798- 1812 ,(2005) , 10.1002/HLCA.200590141
Ming De Wang, Howard Alper, CATALYTIC AND PHOTOLYTIC REACTIONS OF 5,6,7,8-TETRAHYDROINDOLIZINES WITH OXYGEN Tetrahedron Letters. ,vol. 36, pp. 6855- 6858 ,(1995) , 10.1016/0040-4039(95)01437-M
Fernando Coelho, Wanda P. Almeida, Reação de Baylis-Hillman: uma estratégia para a preparação de intermediários multifuncionalizados para síntese orgânica Química Nova. ,vol. 23, pp. 98- 101 ,(2000) , 10.1590/S0100-40422000000100017
No Soo Kim, Jong Ryoo Choi, Jin Kun Cha, A concise, enantioselective synthesis of castanospermine Journal of Organic Chemistry. ,vol. 58, pp. 7096- 7099 ,(1993) , 10.1021/JO00077A034
Chinmay Bhat, Santosh G. Tilve, Recent advances in the synthesis of naturally occurring pyrrolidines, pyrrolizidines and indolizidine alkaloids using proline as a unique chiral synthon RSC Advances. ,vol. 4, pp. 5405- 5452 ,(2014) , 10.1039/C3RA44193H
Silvia Rocchiccioli, Roberta Settambolo, Raffaello Lazzaroni, Domino reaction sequences in the rhodium-catalyzed hydroformylation of 3-acetyl-1-allylpyrrole : a short route to 5,6,7,8-tetrahydroindolizines Journal of Organometallic Chemistry. ,vol. 690, pp. 1866- 1870 ,(2005) , 10.1016/J.JORGANCHEM.2005.01.018
Moira L. Bode, Perry T. Kaye, A new synthesis of indolizines via thermal cyclisation of 2-pyridyl derivatives Journal of The Chemical Society-perkin Transactions 1. pp. 2612- 2613 ,(1990) , 10.1039/P19900002612
Amit N. Pandya, James T. Fletcher, Eric M. Villa, Devendra K. Agrawal, Silver-Mediated Synthesis of Indolizines via Oxidative C-H functionalization and 5- endo-dig cyclization Tetrahedron Letters. ,vol. 55, pp. 6922- 6924 ,(2014) , 10.1016/J.TETLET.2014.10.112