Michael-Type Addition of O-Ethyl-C,O-bis(trimethylsilyl)ketene Acetal and its Application to the Synthesis of α-Ylidene-δ-lactones

Article abstract of DOI:10.1016/0022-328X(87)80302-9

O-Ethyl-C,O-bis(trimethylsilyl)ketene acetal behaves as an active C₂ chainlenghtening unit when with α,β-unsaturated ketones yielding δ-keto-α-trimethylsilylesters with the aid of titanium tetrachloride.The products readily form α-ylidene-δ-lactone derivatives after selective reduction of the ketone carbonyl and subsequent Peterson type olefination.