182008-78-2Relevant articles and documents
Highly stereoselective syntheses of spiroacetal enol ethers, (E)- and (Z)-methoxycarbonylmethylene-1,6-dioxaspiro[4,5]decanes
Toshima, Hiroaki,Aramaki, Hisateru,Furumoto, Yoshinori,Inamura, Shintaro,Ichihara, Akitami
, p. 5531 - 5544 (1998)
(E)- and (Z)-2-methoxycarbonylmethylene-1,6-dioxaspiro[4,5]decanes have been synthesized from an acyclic keto alcohol possessing an alkynoate part via intramolecular conjugate addition. Under thermodynamically controlled conditions using t-BuOK in THF, the (E)-isomer could be obtained in 52:1 ratio. When a catalytic amount of Pd(OAc)2 was used in benzene, the (Z)- isomer could be obtained in 95:1 ratio.
Synthesis of spiroacetal enol ethers via intramolecular conjugate addition of hemiacetal alkoxides to alkynoates
Toshima, Hiroaki,Furumoto, Yoshinori,Inamura, Shintaro,Ichihara, Akitami
, p. 5707 - 5710 (2007/10/03)
(E)- and (Z)-2-Methoxycarbonylmethylene-1,6-dioxaspiro[4.5]decane (12E, 12Z) have been constructed from the acyclic keto alcohol 11a possessing an alkynoate part under the basic conditions. By the thermodynamic control, 12E could be obtained in high selectivity. Under several basic and acidic conditions, 12Z could be isomerized to 12E.