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A Convenient Triisobutylaluminium (TIBAL)-Promoted Johnson-Claisen Approach to γ,δ-Unsaturated Alcohols

Kelly L. Cosgrove, Ross P. McGeary*

*School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia, Email:

K. L. Cosgrove, R. P. McGeary, Synlett, 2009, 1749-1752.

DOI: 10.1055/s-0029-1217382


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 and a subsequent reduction of the ester products in the presence of DIBAL, to give unsaturated γ,δ-primary alcohols in a convenient, one-pot procedure.

see article for more examples

proposed reaction pathway

An Efficient and Solvent-Free Synthesis of Mixed Ortho Esters

K. L. Cosgrove, R. P. McGeary, Synlett, 2008, 2425-2428.

Key Words

Johnson-Claisen Rearrangement, triisobutylaluminium, mixed ortho esters, ketene dimethyl acetal, γ,δ-unsaturated alcohols

ID: J60-Y2009-1930