Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 7, Pages 1287-1295Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201410
Keywords
Synthetic methods; Indium; Alkynes; Regioselectivity; Diastereoselectivity; Propargylation; Sulfinylimines
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CTQ2007-65218, 2010-CSD-2007-00006, CTQ2011-24165]
- Generalitat Valenciana [PROMETEO/2009/039]
- Fondos Europeos para el Desarrollo Regional (FEDER)
- University of Alicante
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The reaction of different chiral imines 3 derived from aldehydes or ketones with the silylated propargyl bromide 4b under sonication in the presence of indium metal led mainly or exclusively to the formation of protected homopropargylamines 5 in a diastereoselective manner. Of special interest are the ketimine derivatives because the new stereocenter has a quaternary configuration. The selective deprotection of the two protecting groups, the silicon and sulfinyl moieties, was easily achieved by conventional methodologies.
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