Journal
TETRAHEDRON LETTERS
Volume 53, Issue 39, Pages 5287-5289Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.07.094
Keywords
Transesterification; High pressure; Sterically hindered alcohols; Amino acid esters; Racemization
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Funding
- Ministry of Science and Higher Education [501/86-DSM-100100]
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A mild, rapid, and efficient method for the solvolysis of sterically hindered esters under high pressure is described. Transesterification is carried out in the presence of DBU at room temperature and at a pressure of 10 kbar to give quantitative conversions within short reaction times. The substrates examined included aromatic and aliphatic esters of sterically hindered alcohols and phenols. An optically pure benzyl ester of phenylalanine was chosen to study racemization of the amino acid esters under high-pressure reaction conditions. (c) 2012 Elsevier Ltd. All rights reserved.
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