An organocatalytic approach to stereoselective synthesis of 2-hydroxyazetidines and 2-hydroxypyrrolidines

作者: Ankita Rai , Lal Dhar S. Yadav

DOI: 10.1016/J.TETLET.2013.04.013

关键词:

摘要: Abstract A straightforward asymmetric synthesis of a new series 2-hydroxyazetidines/2-hydroxypyrrolidines with excellent diastereoselectivity was developed via enamine catalysis using diphenylprolinol silyl ether. The Mannich-type reaction chiral enamines various aldimines/aziridines under mild conditions followed by intramolecular hemiaminalization affords the desired products 2-hydroxyazetidines and 2-hydroxypyrrolidines, respectively, in one-pot operation. scope generality adequately investigated were optimized extensively.

参考文章(109)
Theophil Eicher, Siegfried Hauptmann, Andreas Speicher, The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications ,(1995)
J. A. Joule, K. Mills, Heterocyclic Chemistry at A Glance ,(2013)
Mark Plehiers, Claude Hootelé, Hydroboration of enecarbamates and the synthesis of β-hydroxypiperidine alkaloids Tetrahedron Letters. ,vol. 34, pp. 7569- 7570 ,(1993) , 10.1016/S0040-4039(00)60402-1
Marta Poch, Xavier Verdaguer, Albert Moyano, Miquel A. Pericàs, Antoni Riera, A versatile enantiospecific approach to 3-azetidinols and aziridines Tetrahedron Letters. ,vol. 32, pp. 6935- 6938 ,(1991) , 10.1016/0040-4039(91)80448-F
Francois Couty, Gwilherm Evano, Monica Vargas-Sanchez, Gloria Bouzas, Practical asymmetric preparation of azetidine-2-carboxylic acid. Journal of Organic Chemistry. ,vol. 70, pp. 9028- 9031 ,(2005) , 10.1021/JO0515881
Rafael Pedrosa, Celia Andrés, Javier Nieto, Soledad del Pozo, Diastereoselective Yang Photocyclization Reactions in Solution. Synthesis of Enantiopure Azetidin-3-ol Derivatives Journal of Organic Chemistry. ,vol. 70, pp. 1408- 1416 ,(2005) , 10.1021/JO0481497
Santanu Mukherjee, Jung Woon Yang, Sebastian Hoffmann, Benjamin List, Asymmetric enamine catalysis. Chemical Reviews. ,vol. 107, pp. 5471- 5569 ,(2007) , 10.1021/CR0684016