Tetrahedron p. 5531 - 5544 (1998)
Update date:2022-07-30
Topics:
Toshima, Hiroaki
Aramaki, Hisateru
Furumoto, Yoshinori
Inamura, Shintaro
Ichihara, Akitami
(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.
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