(Chemical Equation Presented) 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. © 2007 American Chemical Society.
Chiral polycyclic ketones via desymmetrization of dihaloolefins / Borsato, Giuseppe; Linden, Anthony; De Lucchi, Ottorino; Lucchini, Vittorio; Wolstenholme, David; Zambon, Alfonso. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 72:11(2007), pp. 4272-4275. [10.1021/jo070222g]
Chiral polycyclic ketones via desymmetrization of dihaloolefins
ZAMBON, Alfonso
2007
Abstract
(Chemical Equation Presented) 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. © 2007 American Chemical Society.
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