Asymmetric Synthesis of Both Enantiomers of N-Protected Epibatidine via Reductive Heck-Type Hetarylation

Jan Christoph Namyslo; Dieter E. Kaufmann

doi:10.1055/s-1999-2719

Synlett 1999; 1999(6): 804-806
DOI: 10.1055/s-1999-2719

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Asymmetric Synthesis of Both Enantiomers of N-Protected Epibatidine via Reductive Heck-Type Hetarylation

Jan Christoph Namyslo^* , Dieter E. Kaufmann

^*Technische Universität Clausthal, Institut für Organische Chemie, Leibnizstr. 6, D-38678 Clausthal-Zellerfeld, Germany; Fax +49 (0) 53 23/72-28 34; E-mail: dieter.kaufmann@tu-clausthal.de

Abstract

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The first enantioselective reductive Heck-type hetarylation of the azabicyclus 3 is presented using the optically active ligands 5-10. This asymmetric reaction provides both enantiomers of the protected trace alkaloid epibatidine in yields typically ranging from 30 to 60% with an enantiomeric excess up to 81%.

asymmetric catalysis - alkaloids - palladium - C-C coupling - eterocycles

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