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  • Title: Organocatalytic asymmetric robinson annulation of alpha,beta-unsaturated aldehydes: applications to the total synthesis of (+)-palitantin.
    Author: Hong BC, Wu MF, Tseng HC, Huang GF, Su CF, Liao JH.
    Journal: J Org Chem; 2007 Oct 26; 72(22):8459-71. PubMed ID: 17919000.
    Abstract:
    The highly enantioselective organocatalytic Robinson annulation of alpha,beta-unsaturated aldehydes was achieved, catalyzed by l-proline and trialkylamines and providing the formal [4 + 2] cycloaddition adducts. Additionally, in some examples in the catalysis with diarylpyrrolinol silyl ethers, the reactions afforded the [4 + 2] adducts with high enantioselectivity (>99.5% ee). The structure of the adduct, obtained from the reaction of 3-methylbut-2-enal and (E)-3-(2-nitrophenyl)acrylaldehyde, was confirmed by X-ray analysis. The absolute configurations of some [4 + 2] cycloadducts were investigated, and the methodology was applied in the synthesis of (+)-palitantin.
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