Catalytic Enantioselective Addition of Dialkylzinc Reagents to N-Acylpyridinium Salts


  • This research was financially supported by the Dutch Ministry of Economic Affairs. M.A.F.-I. is grateful to the Spanish Ministry of Education and Science for a postdoctoral fellowship. Dr. S. R. Harutyunyan is thanked for helpful discussions.


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A pinch of salt: The first catalytic addition of dialkylzinc reagents to N-acylpyridinium salts with good yields and excellent enantioselectivities uses a copper–(S)-L complex as the catalyst. The versatility of the method is illustrated in the formal synthesis of the alkaloid (R)-coniine. Bn=benzyl, Tf=trifluoromethanesulfonyl.