Chiral Polycyclic Ketones via Desymmetrization of Dihaloolefins

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...

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Veröffentlicht in:Journal of organic chemistry 2007-05, Vol.72 (11), p.4272-4275
Hauptverfasser: Borsato, Giuseppe, Linden, Anthony, De Lucchi, Ottorino, Lucchini, Vittorio, Wolstenholme, David, Zambon, Alfonso
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Alkenes - chemistry
Catalysis
Chemistry
Ephedrine - chemistry
Exact sciences and technology
Halogens - chemistry
Hydrolysis
Ketones - chemistry
Molecular Structure
Norbornanes - chemistry
Organic chemistry
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Preparations and properties
Stereoisomerism
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Beschreibung
Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070222g