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.2007 May 25;72(11):4272-5.
doi: 10.1021/jo070222g. Epub 2007 May 3.

Chiral polycyclic ketones via desymmetrization of dihaloolefins

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Chiral polycyclic ketones via desymmetrization of dihaloolefins

Giuseppe Borsato et al. J Org Chem..

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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