Indium-mediated diastereoselective allylation of N-tert-butanesulfinyl imines derived from α-ketoesters
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Title: | Indium-mediated diastereoselective allylation of N-tert-butanesulfinyl imines derived from α-ketoesters |
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Authors: | Maciá, Edgar | Foubelo, Francisco | Yus, Miguel |
Research Group/s: | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Diastereoselective addition | Allylation | Chiral sulfinyl imines | Enantioenriched α-amino esters | α-Methylene-γ-butyrolactams |
Knowledge Area: | Química Orgánica |
Issue Date: | 6-Oct-2016 |
Publisher: | Elsevier |
Citation: | Tetrahedron. 2016, 72(40): 6001-6010. doi:10.1016/j.tet.2016.07.020 |
Abstract: | The indium-mediated allylation of α-aldimino and -ketimino esters 3 with allylic bromides proceeds with high diastereoselectivity to yield homoallylic α-amino ester derivatives 5, in both THF and water as solvents. The reactions are diastereospecific, the stereochemical outcome depending on the configuration of both the sulfur atom of the sulfinyl group and the Cdouble bond; length as m-dashN double bond. Of particular interest are the reaction products using ethyl bromomethylacrylate as allylating reagent because amino diesters are obtained, which can be easily transformed into enantiomerically pure α-methylidene-γ-butyrolactams 6 with an alkoxycarbonyl group on the ring bearing the nitrogen atom. |
Sponsor: | We thank the continued financial support from our Ministerio de Ciencia e Innovación (MCINN; projects CONSOLIDER INGENIO 2010-CDS2007-00006, CTQ2011-24165), the Ministerio de Economía y Competitividad (MINECO; project CTQ2014-53695-P, CTQ2014-51912-REDC), FEDER, the Generalitat Valenciana (PROMETEO 2009/039, PROMETEOII/2014/017) and the University of Alicante. |
URI: | http://hdl.handle.net/10045/58079 |
ISSN: | 0040-4020 (Print) | 1464-5416 (Online) |
DOI: | 10.1016/j.tet.2016.07.020 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2016 Elsevier Ltd. |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1016/j.tet.2016.07.020 |
Appears in Collections: | INV - SINTAS - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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2016_Macia_etal_Tetrahedron_final.pdf | Versión final (acceso restringido) | 957,28 kB | Adobe PDF | Open Request a copy |
2016_Macia_etal_Tetrahedron_accepted.pdf | Accepted Manuscript (acceso abierto) | 676,51 kB | Adobe PDF | Open Preview |
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