Enantioselective synthesis of bridgehead hydroxyl bicyclo[2.2.2]octane derivatives via asymmetric allylindation
Författare
Summary, in English
A recent new strategy for the transformation of mono-dioxolane protected 1,3-cyclohexadione into bridgehead hydroxyl bicyclo[2.2.2]octane derivatives, based on allylindation followed by ozonolysis and intramolecular aldol addition, was modified to include asymmetric allylindation. This enabled the first enantioselective synthesis of (1R,4R,6S)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2 ]octan-2-one and (1S,4S,6R)-endo-4-(tert-butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2 ]octan-2-one in high enantiomeric excess. Issues concerning the non-reproducibility of the asymmetric allylindation were also addressed. (c) 2006 Elsevier Ltd. All rights reserved.
Avdelning/ar
Publiceringsår
2006
Språk
Engelska
Sidor
410-415
Publikation/Tidskrift/Serie
Tetrahedron: Asymmetry
Volym
17
Issue
3
Dokumenttyp
Artikel i tidskrift
Förlag
Elsevier
Ämne
- Organic Chemistry
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 0957-4166