Stereoselective synthesis of optically active cyclopenta[c]pyridines and tetrahydropyridines
作者： Serdar Sezer , Yasemin Gümrükçü , İrem Bakırcı , M. Yağız Ünver , Cihangir Tanyeli
DOI: 10.1016/J.TETASY.2012.04.016
关键词:
摘要: Abstract The intramolecular Pauson–Khand and ring closing metathesis (RCM) reactions of nitrogen containing chiral enynes dienes are described. enyne diene systems comprised N-propargylated N-allylated units constructed on homoallylic or homopropargylic alcohol backbones, respectively, via S N 2 and/or modified Mitsunobu reactions. racemic derivatives were successfully resolved in high ee (93–99%) by applying chemoenzymatic methods using various lipases such as PS-C II, Lipozyme, CAL-B. Each enantiomerically enriched afforded the most conformationally stable diastereomeric cyclopenta[ c ]pyridine system sole product, whereas gave tetrahydropyridine a result RCM reactions, respectively.
sci-hub.se 参考文章(58)
Louis S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules ,(1999)
N. E. Schore, M. C. Croudace, Preparation of bicyclo[3.3.0]oct-1-en-3-one and bicyclo[4.3.0]non-1(9)-en-8-one via intramolecular cyclization of .alpha.,.omega.-enynes Journal of Organic Chemistry. ,vol. 13, pp. 5436- 5438 ,(1981) , 10.1021/JO00339A046
Philip Magnus, Lawrence M. Principe, Origins of 1,2- and 1,3-stereoselectivity in dicobaltoctacarbonyl alkene-alkyne cyclizations for the synthesis of substituted bicyclo[3.3.0]octenones. Tetrahedron Letters. ,vol. 26, pp. 4851- 4854 ,(1985) , 10.1016/S0040-4039(00)94968-2
Ahmed Kamal, J. Surendranadha Reddy, E. Vijaya Bharathi, D. Dastagiri, Base-free monosulfonylation of amines using tosyl or mesyl chloride in water Tetrahedron Letters. ,vol. 49, pp. 348- 353 ,(2008) , 10.1016/J.TETLET.2007.11.044
Leticia Pérez-Serrano, Luis Casarrubios, Gema Domínguez, Javier Pérez-Castells, Pauson-Khand Reaction Induced by Molecular Sieves † Organic Letters. ,vol. 1, pp. 1187- 1188 ,(1999) , 10.1021/OL990856C
Yining Ji, Antoni Riera, Xavier Verdaguer, Saline Intermolecular Pauson–Khand Reactions of Propargyl Amine European Journal of Organic Chemistry. ,vol. 2011, pp. 1438- 1442 ,(2011) , 10.1002/EJOC.201001617
Yvonne Kavanagh, Matthew O'Brien, Paul Evans, Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton Tetrahedron. ,vol. 65, pp. 8259- 8268 ,(2009) , 10.1016/J.TET.2009.07.060
Ana Z. Gonzalez, John A. Soderquist, β-Silylated Homopropargylic Amines via the Asymmetric Allenylboration of Aldimines Organic Letters. ,vol. 9, pp. 1081- 1084 ,(2007) , 10.1021/OL070074G
Takumichi Sugihara, Mamiko Yamada, Masahiko Yamaguchi, Mugio Nishizawa, The Intra- and Intermolecular Pauson-Khand Reaction Promoted by Alkyl Methyl Sulfides Synlett. ,vol. 1999, pp. 771- 773 ,(1999) , 10.1055/S-1999-2745
Merve Çayir, Sema Demirci, Serdar Sezer, Cihangir Tanyeli, Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction Tetrahedron-asymmetry. ,vol. 22, pp. 1161- 1168 ,(2011) , 10.1016/J.TETASY.2011.07.003