Stereoselective synthesis of bicyclo[3.3.0]oct-1-en-3-one derivatives
✍ Scribed by F. Camps; J. Coll; J.M. Moretó; J. Torras
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 191 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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Imramolccular Paoson-Khand reactions of M-enynes 3a-c with a methylenecyclopropane terminator and a cbii acetal moiety adjacent to the triple bond gave spiro(cyclopropaae-l,4'-bicyclo[3.3.0]oct-l-en-3-ones) 5a-c in good yields with a diaste~lcctivity of up to 6.411. 'Ihe major diastenxmer of 5b was
Bicyclo[3.3.0]oct-2-ene derivatives with high optical purities (87-99s e.e) were obtained by asymmetric elimination of the trifluoromethanesulfonates(l0, 11, 12) by chiral N,N-dimethyl-1-phenethylamine.
Annulation of double donating molecules like dimethyl glutaconate as well as dimethyl 3-oxoglutarate to 4-acetoxy-2-cyclopenten-I -one opens stereoselective routes to various bicyclo[3.3.0]octanone derivatives. ## Cyclopentenon -Derivate, XI I! -Stereoselektive Wege zu Bicyclo~3.3.0Joctanonen Die