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2005
Ester hydrolysis
O 0316
A Mild and Selective Method for the Hydrolysis of Esters with Trimethyltin Hy— The new method is also applicable to substrates sensitive to epimerization.
24- 057 droxide.
Even the Fmoc protecting group is not decomposed during hydrolysis. The method is
efficient for the cleavage of methyl, ethyl, allyl, and benzyl esters but ineffective for
pivaloate esters. Methyl esters are preferentially hydrolyzed over isopropyl and ethyl
esters. In contrast to other known methods, hydrolysis of (IX) results in the formation
of the corresponding carboxylic acid without loss of stereochemistry. The results are of
interest in connection with the preparation of the thiopeptide antibiotic thiostrepton.
— (NICOLAOU*, K. C.; ESTRADA, A. A.; ZAK, M.; LEE, S. H.; SAFINA, B. S.;
Angew. Chem., Int. Ed. 44 (2005) 9, 1378-1382; Dep. Chem., Scripps Res. Inst.,
San Diego, La Jolla, CA 92037, USA; Eng.) — S. Adam
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