Synthesis of spiroacetal enol ethers via intramolecular conjugate addition of hemiacetal alkoxides to alkynoates

( E)- and ( Z)-2-Methoxycarbonylmethylene-1,6-dioxaspiro[4.5]decane ( 12 E, 12 Z ) have been constructed from the acyclic keto alcohol 11a possessing an alkynoate part under the basic conditions. By the thermodynamic control, 12 E could be obtained in high selectivity. Under several basic and acidic...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 1996-08, Vol.37 (32), p.5707-5710
Main Authors: Toshima, Hiroaki, Furumoto, Yoshinori, Inamura, Shintaro, Ichihara, Akitami
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:( E)- and ( Z)-2-Methoxycarbonylmethylene-1,6-dioxaspiro[4.5]decane ( 12 E, 12 Z ) have been constructed from the acyclic keto alcohol 11a possessing an alkynoate part under the basic conditions. By the thermodynamic control, 12 E could be obtained in high selectivity. Under several basic and acidic conditions, 12 Z could be isomerized to 12 E. ( E)- and ( Z)-2-Methoxycarbonylmethylene-1,6-dioxaspiro[4.5]decane ( 12E and 12Z ) have been constructed from the acyclic keto alcohol 11a possessing an alkynoate part under basic conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01206-3