Electroreduction of series of γ-ethynl ketones in dimethylformamide gave the cyclization products, 2-methylenecyclopentanols, as the sole product in excellent yeilds. furthermore, this electrochemical techniqe was applied to a new synthesis of bicyclic alcohols with an exocyclic double bond adjacent to a bridgehed hydroxy group.
Aus den Cyclohexenon‐epoxiden (I) entstehen nach Eschenmoser die Acetylenketone (IIa)‐(IIe) bzw. (IIIa) und (IIIb), aus den bicyclischen Methylenepoxiden (IV) die Cycloalkanon‐acetylene (V).
Der auf dem beschriebenen Weg synthetisierte Rhodiumkomplex (IV) katalysiert die asymmetrische Hydrosilylierung einer Vielzahl von Ketonen (V) mit (VI) zu den Siloxyverbindungen (VII), aus denen die Alkohole (VIII) zugänglich sind.
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