Journal
TETRAHEDRON LETTERS
Volume 55, Issue 35, Pages 4959-4961Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.07.015
Keywords
Zinc acetylides; Nitrones; Silyl triflates; Propargyl amines
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Funding
- National Science Foundation RUI program [CHE-1057591]
- Camille and Henry Dreyfus Foundation
- University of Richmond College of Arts and Sciences
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1057591] Funding Source: National Science Foundation
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Terminal alkynes readily form zinc acetylides in the presence of iPr(2)NEt and 20 mol % ZnBr2, then attack N-phenyl nitrones activated by trimethylsilyl trifluoromethanesulfonate. Deprotection with aqueous acid yields N-hydroxyl propargylamine. Yields are generally high for nitrones derived from aromatic aldehydes. Control experiments suggest that silyl triflate has a significant accelerating effect upon the reaction. (C) 2014 Elsevier Ltd. All rights reserved.
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