Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 23, Pages 4067-4076Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600612
Keywords
Synthetic methods; Isomerization; Imines; Epoxides; Allylation; Lewis acids
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MCINN) [CONSOLIDER INGENIO 2010-CDS2007-00006, CTQ2011-24165]
- Ministerio de Economia y Competitividad (MINECO) [CTQ2014-53695-P, CTQ2014-51912-REDC]
- Fondos Europeos para el Desarrollo Regional (FEDER)
- Generalitat Valenciana [PROMETEO 2009/039, PROMETEOII 2014/017]
- University of Alicante, Spain
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The reaction of epoxides with tert-butanesulfinamide in the presence of a Lewis acid, such as erbium triflate or boron trifluoride-diethyl ether, in THF as solvent, under microwave or thermal activation, produces N-tert-butylsulfinylimines in reasonable yields. Aromatic and gem-disubstituted and trisubstituted alkyl epoxides performed better than mono-alkyl-substituted compounds. After imine formation, a subsequent indium-promoted allylation can be carried out in the same reaction flask in a single synthetic operation leading to homoallylamine derivatives with generally high yields.
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