Enantiospecific synthesis and chiroptical properties of bicyclic enones

Summary, in English

The enantiospecific synthesis of several bicyclic enones starting from enantiomerically pure (+)-(1S,5S)-bicyclo[3.3.1]-nonane-2,6-dione (1) was accomplished. The target enones 7-9 were obtained in high yield and purity by using a catalytic amount of benzeneselenic anhydride. (+)-(1S,5R)-bicy-clo[3.3.1]inonane-2,3,6-trione was obtained from diketone 1 by alpha-hydroxylation involving the use of iodine under basic conditions. The reaction included a ring closure/reopening sequence via oxatricyclo[4.3.1.0(3,8)]decane-10-one. It was shown that the latter triketone exists in enone/enol form.

• Författare: Edvinas Orentas; Gintautas Bagdziunas; Ulf Berg; Albinas Zilinskas; Eugenijus Butkus
• Avdelning/ar: Centrum för analys och syntes
• Publiceringsår: 2007
• Språk: Engelska
• Sidor: 4251-4256
• Publikation/Tidskrift/Serie: European Journal of Organic Chemistry
• Issue: 25
• Länkar: http://dx.doi.org/10.1002/ejoc.200700241
• Dokumenttyp: Artikel i tidskrift
• Förlag: John Wiley & Sons Inc.
• Ämne: Organic Chemistry
• Nyckelord: chirality; CD spectroscopy; chromopbores; enones; enantiospecific synthesis
• Status: Published
• ISBN/ISSN/Övrigt: ISSN: 1434-193X