ChemInform Abstract: Enantiospecific Generation of anti-Aldol Adducts via Conjugate Addition to 5-Methylene-1,3-dioxan-4-ones.
Abstract
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ChemInform Abstract
Michael addition reactions to the exocyclic olefinic double bond of the optically pure dioxane (I) are investigated. The reaction with cuprates, Stryker′s reagent or copper-mediated addition of Grignard reagents [cf. (V)] proceeds with poor diastereoselectivity. However, radical addition of alkyl iodides leads to the trans products (VIII) with complete diastereoselectivity. The adducts [cf. (VIIIa)] can be easily opened under reductive and acidic conditions.
