2‑Pyridinyl‑N‑(2,4-difluorobenzyl)aminoethyl Group As Thermocontrolled Implement for Protection of Carboxylic Acids
journal contributionposted on 23.06.2016 by Jolanta Brzezinska, Agnieszka Witkowska, Sandra Bałabańska, Marcin K. Chmielewski
Any type of content formally published in an academic journal, usually following a peer-review process.
A thermolabile protecting group strategy for carboxylic acids is expanded. Thermosensitive esters are readily prepared using a known procedure, and their stability under neutral condition is investigated. Effective thermolytic deprotection initiated only by temperature for different carboxylic acids is demonstrated, and the compatibility of a thermolytic protecting group with acidic and basic protecting groups in an orthogonal protection strategy is also presented. This study showed interesting correlations between the pKa of acids and the deprotection rate of their well-protected moieties.