A Convenient Triisobutylaluminium (TIBAL)-Promoted Johnson-Claisen Approach to γ,δ-Unsaturated Alcohols
Author(s)
L. Cosgrove, Kelly
P. McGeary, Ross
Griffith University Author(s)
Year published
2009
Metadata
Show full item recordAbstract
Mixed ortho esters derived from allylic alcohols undergo methanol elimination in the presence of triisobutylaluminium (TIBAL) at room temperature to form mixed ketene acetals. TIBAL then promotes immediate Claisen rearrangement of these intermediates, and subsequent reduction of the ester products, to give unsaturated ?,d-primary alcohols in a convenient, one-pot procedure.Mixed ortho esters derived from allylic alcohols undergo methanol elimination in the presence of triisobutylaluminium (TIBAL) at room temperature to form mixed ketene acetals. TIBAL then promotes immediate Claisen rearrangement of these intermediates, and subsequent reduction of the ester products, to give unsaturated ?,d-primary alcohols in a convenient, one-pot procedure.
View less >
View less >
Journal Title
Synlett
Volume
2009
Issue
11
Subject
Organic Chemical Synthesis
Medicinal and Biomolecular Chemistry
Organic Chemistry