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Stereoselective synthesis of α-methylenecyclopentenones via a Diels–Alder/retro-Diels–Alder protocol
Weerachai Phutdhawong Gedsirin Eksinitkun Stephen G. Pyne Anthony C. Willis Waya S. Phutdhawong 《Tetrahedron》2013
A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels–Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermediate. The addition of propyllithium or octyllithium to the key intermediate followed by a retro-Diels–Alder reaction furnished α-methylenecyclopentenones bearing a γ-propyl or γ-octyl side chain, respectively, in moderate yields and as single geometric isomers. 相似文献
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