Horner Emmons olefination
Diastereoselective aprotic Michael cascade reaction
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Starting from the easily accesible chiral aldehyde 2, we obtained enantiomerically pure (Z)- and (E)-α,-chloro-α,β-unsaturated esters 4c in good yields by olefination reactions. (Z)-and (E)-4c were allowed to react with the kinetically controlled generated lithium dienolate Li-7 to give the enantiomerically pure tricyclo[3.2.1.02,7]octanes 8 and 9, respectively. The „push-pull“ substituted cyclopropane moiety of 8 was opened to give solely bicyclo[3.2.1]octane 10.
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