Chiral polycyclic ketones via desymmetrization of dihaloolefins.
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.
Borsato
Giuseppe
G
Dipartimento di Scienze Ambientali and Dipartimento di Chimica, Università Ca' Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy. gborsato@unive.it
Linden
Anthony
A
Lucchi
Ottorino De
OD
Lucchini
Vittorio
V
Wolstenholme
David
D
Zambon
Alfonso
A
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004809:Ephedrine / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D006868:Hydrolysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D006219:Halogens; D007659:Ketones; D009636:Norbornanes; D011083:Polycyclic Compounds; D004809:Ephedrine