Synthesis, Table of Contents PSP© Georg Thieme Verlag Stuttgart · New YorkStereoselective Synthesis of meso- and cis-2,6-Diarylpiperidin-4-ones Catalyzed by l-ProlineFernando Aznar*, Ana-Belén García, Noelia Quiñones, María-Paz CabalUnidad Asociada al C.S.I.C., Instituto Universitario de Química Organometálica ‘Enrique Moles’, Universidad de Oviedo, C/ Julián Clavería 8, 33006 Oviedo, SpainFax: +34(98)5103446; e-Mail: pcabal@uniovi.es; Recommend Article Abstract Buy Article All articles of this category Abstract A convenient stereoselective preparation of meso- and cis-2,6-diarylpiperidin-4-ones has been developed by aza-Diels-Alder reaction catalyzed by l-proline from simple and commercially available starting materials. Key words 2,6-diarylpiperidin-4-ones - organocatalysis - l-proline - aza-Diels-Alder - nitrogen heterocycles Full Text References References <A NAME="RZ16207SS-1A">1a</A> Rubiralta M. Giralt E. Díez A. Piperidine. Structure, Preparation, Reactivity and Synthetic Applications of Piperidine and its Derivatives Elsevier; Amsterdam: 1991. <A NAME="RZ16207SS-1B">1b</A> Bailey PD. Smith PD. Morgan KM. Rosair GM. Tetrahedron Lett. 2002, 43: 1071 <A NAME="RZ16207SS-1C">1c</A> Amat M. Llor N. Hidalgo J. Escolano C. Bosch J. J. Org. Chem. 2003, 68: 1919 <A NAME="RZ16207SS-2A">2a</A> Tortolani DR. Poss MA. Org. Lett. 1999, 1: 1261 <A NAME="RZ16207SS-2B">2b</A> Weintraub PM. Sabol JS. Kane JM. Borcherding DR. Tetrahedron 2003, 59: 2953 <A NAME="RZ16207SS-2C">2c</A> Jagt RBC. Vries JG. Feringa BL. Minnaard AJ. Org. Lett. 2005, 7: 2433 <A NAME="RZ16207SS-3A">3a</A> Ganellin CR. Spickett RG. J. Med. Chem. 1965, 8: 619 <A NAME="RZ16207SS-3B">3b</A> Ishimaru K. Kojima T. J. Chem. Soc., Perkin Trans. 1 2000, 2105 <A NAME="RZ16207SS-3C">3c</A> Rameshkumar N. Veena A. Ilavarasan R. Adiraj M. Shanmugapandiyan P. Sridhar SK. Biol. Pharm. Bull. 2003, 26: 188 <A NAME="RZ16207SS-3D">3d</A> Ramalingan C. Balasubramanian S. Kabilan S. Vasudevan M. Eur. J. Med. Chem. 2004, 34: 527 <A NAME="RZ16207SS-4A">4a</A> Baliah V. Jeyaraman R. Chandrasekaran L. Chem. Rev. 1983, 83: 379 <A NAME="RZ16207SS-4B">4b</A> Vijayabaskar V. Perumal S. Devanathan VC. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1995, 34: 649 <A NAME="RZ16207SS-4C">4c</A> Ciblat S. Besse P. Canet JL. Troin Y. Veschambre H. Gelas J. Tetrahedron: Asymmetry 1999, 10: 2225 <A NAME="RZ16207SS-4D">4d</A> Ma D. Sun H. Org. Lett. 2000, 2: 2503 <A NAME="RZ16207SS-4E">4e</A> Davis FA. Chao B. Rao A. Org. Lett. 2001, 3: 3169 <A NAME="RZ16207SS-4F">4f</A> Ma D. Ma N. Tetrahedron Lett. 2003, 44: 3963 <A NAME="RZ16207SS-4G">4g</A> Davis FA. Rao A. Carroll PJ. Org. Lett. 2003, 5: 3855 <A NAME="RZ16207SS-5A">5a</A> List B. Synlett 2001, 1675 <A NAME="RZ16207SS-5B">5b</A> List B. Tetrahedron 2002, 58: 5573 <A NAME="RZ16207SS-5C">5c</A> Notz W. Tanaka F. Barbas CF. Acc. Chem. Res. 2004, 37: 580 <A NAME="RZ16207SS-5D">5d</A> Sundén H. Ibrahem I. Eriksson L. Córdova A. Angew. Chem. Int. Ed. 2005, 44: 4877 <A NAME="RZ16207SS-6A">6a</A> Barluenga J. Aznar F. Cabal M.-P. Valdés C. J. Org. Chem. 1993, 58: 3391 <A NAME="RZ16207SS-6B">6b</A> Barluenga J. Aznar F. Ribas C. Valdés C. Fernández M. Cabal M.-P. Trujillo J. Chem. Eur. J. 1996, 2: 805 <A NAME="RZ16207SS-6C">6c</A> García A.-B. Valdés C. Cabal M.-P. Tetrahedron Lett. 2004, 45: 4357 <A NAME="RZ16207SS-7">7</A> Aznar F. García A.-B. Cabal M.-P. Adv. Synth. Catal. 2006, 348: 2443 <A NAME="RZ16207SS-8">8</A> Alcaide B. Almendros P. Alonso JM. Aly MF. Org. Lett. 2001, 3: 3781 <A NAME="RZ16207SS-9">9</A> Drake NL. Allen P. Org. Synth. Coll. Vol. I John Wiley & Sons; London: 1932. p.77 <A NAME="RZ16207SS-10A">10a</A> For the preparation of N-alkylimines, see: Look GC. Murphy MM. Campbell DA. Gallop MA. Tetrahedron Lett. 1995, 36: 2937 <A NAME="RZ16207SS-10B">10b</A> For the preparation of N-arylimines, see: Bigelow LA. Eatough H. Org. Synth. Coll. Vol. I John Wiley & Sons; London: 1932. p.80