Abstract
The development of a new, synthetically useful methylenecyclohexane annulation method is described. Transmetallation (MeLi, tetrahydrofuran, −78 °C) of 5-chloro-2-trimethylstannyl-1-pentene (8) affords the novel bifunctional reagent 5-chloro-2-lithio-1-pentene (9), which, at temperatures higher than approximately −50 °C, self-destructs to give methylenecyclobutane (14). Reagent 9 can be converted into the Grignard reagent 10 and the organocopper(I) species 15. Conjugate addition of 10 and 15 to a number of cyclic enones (16–22), followed by intramolecular alkylation of the resultant adducts (23–29), produces the corresponding methylenecyclohexane annulation products (30–40).
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