Dynamic Kinetic Resolution and Desymmetrization of Enantiotopic Groups by Cyclodehydration of Racemic or Prochiral δ-Oxoesters with (R)-Phenylglycinol: Enantioselective Synthesis of Piperidines
Mercedes Amat Prof. Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorMargalida Cantó Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorNúria Llor Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorViviana Ponzo Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorMaria Pérez
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorJoan Bosch Prof. Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorMercedes Amat Prof. Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorMargalida Cantó Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorNúria Llor Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorViviana Ponzo Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorMaria Pérez
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorJoan Bosch Prof. Dr.
Laboratory of Organic Chemistry, Faculty of Pharmacy University of Barcelona Av. Joan XXIII s/n, 08028-Barcelona (Spain) Fax: (+34) 93-402-45-39
Search for more papers by this authorThis work was supported by the DGICYT, Spain (BQU2000-0651), and the CUR, Generalitat de Catalunya (2001SGR-0084). We also thank the Ministry of Education, Culture, and Sport for fellowships to M.C. and M.P., as well as the CICYT, Spain, for a postdoctoral fellowship to V.P.
Graphical Abstract
Enantiotope Estergruppen werden desymmetrisiert bei der Cyclodehydrierung prochiraler δ-Oxodiester mit (R)-Phenylglycinol. Diese Reaktion lässt sich auch auf racemische δ-Oxodiester erweitern, die in einem Tandemprozess aus dynamischer kinetischer Racematspaltung und diastereoselektiver Differenzierung reagieren (siehe Schema). Die erhaltenen bicyclischen Lactame sind präparativ nützlich für die Herstellung pharmakologisch bedeutsamer enantiomerenreiner Piperidinderivate.
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