Author:
Piers Edward,Yeung Bik Wah Anissa,Fleming Fraser F.
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).
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
27 articles.
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