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.
Chiral Polycyclic Ketones via Desymmetrization of Dihaloolefins
BORSATO, Giuseppe;DE LUCCHI, Ottorino;LUCCHINI, Vittorio;
2007-01-01
Abstract
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.
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