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Synlett 1999; 1999(6): 804-806
DOI: 10.1055/s-1999-2719
DOI: 10.1055/s-1999-2719
letter
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Asymmetric Synthesis of Both Enantiomers of N-Protected Epibatidine via Reductive Heck-Type Hetarylation
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Publication History
Publication Date:
31 December 1999 (online)
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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