Journal
TETRAHEDRON LETTERS
Volume 55, Issue 10, Pages 1693-1696Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.01.065
Keywords
Mitsunobu reaction; 3-Hydroxyisoxazole; 3-isoxazolol, isoxazole-3-one; ambident (pro-)nucleophile; Regioselective; Bioisostere
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Funding
- University of Maryland School of Pharmacy
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Regiochemical control in the functionalization of ambident nucleophiles is of particular interest in organic chemistry. Herein, we demonstrate that O-alkylation of ambident 3-hydroxyisoxazoles, which are heterocyclic bioisosteres of carboxylic acids, predominates under Mitsunobu conditions. In several cases, excellent O-regioselectivity (>= 95%) was observed. It is noteworthy that reactions were complete within 15 min at room temperature. Furthermore, the conditions are compatible with a range of alcohols that cover all of the typical protecting groups for the 3-hydroxyisoxazole motif, providing milder, simpler and less hazardous protocols to those commonly followed in the literature. (C) 2014 Elsevier Ltd. All rights reserved.
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