Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5273621 | Tetrahedron Letters | 2012 | 4 Pages |
Abstract
Yield lowering C-silylation was found to be inevitable in all the six tested examples of stoichiometric LDA/TMSCl promoted Ireland-Claisen rearrangement of secondary allyl acetates. In order to circumvent this problem, a higher yielding protocol was devised after the isolated by-products were found to be excellent substrates for further rearrangement. Thus, excessive LDA/TMSCl was applied to achieve complete 3,3â²-sigmatropic shift of the substrates, and the resulting mixtures of normal and α-silylated γ,δ-unsaturated carboxylic acids was then desilylated by one-pot application of TBAF.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Di Liu, Xiaoming Yu,