A NOVEL FRAGMENTATION REACTION OF AN α,β-EPOXYCYCLOPENTANONE. STEREOSELECTIVE FORMATION OF TRISUBSTITUTED E-DOUBLE BOND

Autor: Tsuzuki, Kazuo, Hashimoto, Hisanobu, Shirahama, Haruhisa, Matsumoto, Takeshi
Zdroj: Chemistry Letters; December 1977, Vol. 6 Issue: 12 p1469-1472, 4p
Abstrakt: cis-1,6a-Epoxy-3a-methyloctahydropentalen-2-one readily undergoes fragmentation to give stereoselectively methyl (E)-3-methyl-7-oxo-2-octenoate in 75% yield, on treatment with a catalytic amount of sodium carbonate in methanol. A pericyclic mechanism is suggested for the new ring opening reaction.
Databáze: Supplemental Index