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Chiral Polycyclic Ketones via Desymmetrization of Dihaloolefins

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posted on 25.05.2007, 00:00 by Giuseppe Borsato, Anthony Linden, Ottorino De Lucchi, Vittorio Lucchini, David Wolstenholme, Alfonso Zambon
3-Chloronorbornenone (R)-1a (98% ee) was obtained from trichloronorbornene 5 in two steps by the in situ generation of dichloronorbornadiene 2a with t-BuOK and desymmetrization with (−)-ephedrine, followed by hydrolysis with PPTS. The generality of this desymmetrization with (−)-ephedrine was tested with dibromonorbornadiene 2c and other substituted dichloronorbornadienes.