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Use of hindered silyl ethers as protecting groups for the non-aldol aldol process
Michael E Jung1, Barbara Hoffmann, Bernhard Rausch
1Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu
Organic Letters
|August 15, 2003
Abstract:
[reaction: see text] Bulky epoxy bis-silyl ethers, e.g., 15, derived from 5-trialkylsilyloxy-2-alken-1-ols by epoxidation and silylation were treated with TMSOTf to afford non-aldol aldol rearrangement products, the 3,5-bis(silyloxy)alkanals, e.g., 16, with little to none of the corresponding tetrahydrofurans.