HIGHLY STEREOSELECTIVE SYNTHESES OF SPIROACETAL ENOL ETHERS, METHOXYCARBONYLMETHYLENE-1,6-DIOXASPIRO[4.5]DECANE AND METHOXYCARBONYLMETHYLENE-1,6-DIOXASPIRO[4.5]DECANE

Authors
TOSHIMA H ARAMAKI H FURUMOTO Y INAMURA S ICHIHARA A
Citation
H. Toshima et al., HIGHLY STEREOSELECTIVE SYNTHESES OF SPIROACETAL ENOL ETHERS, METHOXYCARBONYLMETHYLENE-1,6-DIOXASPIRO[4.5]DECANE AND METHOXYCARBONYLMETHYLENE-1,6-DIOXASPIRO[4.5]DECANE, Tetrahedron, 54(21), 1998, pp. 5531-5544
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
21
Year of publication
1998
Pages
5531 - 5544
Database
ISI
SICI code
0040-4020(1998)54:21<5531:HSSOSE>2.0.ZU;2-P
Abstract
(E)- and ethoxycarbonylmethylene-1,6-dioxaspiro[4.5]decanes have been synthesized from an acyclic keto alcohol possessing an alkynoate part via intramolecular conjugate addition. Under thermodynamically control led conditions using t-BuOK in THF, the (E)-isomer could be obtained i n 52:1 ratio. When a catalytic amount of Pd(OAc)(2) was used in benzen e, the (Z)isomer could be obtained in 95:1 ratio. (C) 1998 Elsevier Sc ience Ltd. All rights reserved.