92490-58-9Relevant academic research and scientific papers
Bifunctional conjunctive reagents: 5-chloro-2-lithio-1-pentene and related substances. A methylenecyclohexane annulation method
Piers, Edward,Yeung, Bik Wah Anissa,Fleming, Fraser F.
, p. 280 - 286 (2007/10/02)
The development of a new, synthetically useful methylenecyclohexane annulation method is described.Transmetalation (MeLi, tetrahydrofuran, -78 deg 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 deg 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).
5-Chloro-2-lithio-1-pentene and Related Reagents. Efficient Methylenecyclohexane Annulation Sequences
Piers, Edward,Yeung, Bik Wah Anissa
, p. 4567 - 4569 (2007/10/02)
5-Chloro-2-lithio-1-pentene (7), obtained by transmetalation of the (trimethylstannyl)alkene 11, can be converted into the corresponding Grignard and organocopper reagents.Conjugate addition of the latter species to the enones 13-19, followed by ring clos
