Regioselective and stereoselective reductive cleavage of 1,7-dioxaspiro[5.5]undecane alcohols

Lewis acid -promoted triethylsilane reduction of 6,6-spiroketal alcohols produces cis-2,6-disubstituted tetrahydropyrans with excellent regioselectivity and stereocontrol. An appended alcohol allows bidentate coordination of the Lewis acid to selectively activate one CO bond of the anomeric center...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 1996-08, Vol.37 (32), p.5649-5652
Main Authors: Crimmins, Michael T, Rafferty, Stephen W
Format: Article
Language:English
Subjects:
7-dixaspiroundecanes
Reductive cleavage
spiroketals
tetrahydropyrans
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:Lewis acid -promoted triethylsilane reduction of 6,6-spiroketal alcohols produces cis-2,6-disubstituted tetrahydropyrans with excellent regioselectivity and stereocontrol. An appended alcohol allows bidentate coordination of the Lewis acid to selectively activate one CO bond of the anomeric center toward reductive cleavage. Lewis acid -promoted triethylsilane reduction of 6,6-spiroketal alcohols produces cis-2,6-disubstituted tetrahydropyrans with excellent regioselectivity and stereocontrol. An appended alcohol allows bidentate coordination of the Lewis acid to selectively activate one CO bond of the anomeric center toward reductive cleavage.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01196-3