Journal
TETRAHEDRON
Volume 76, Issue 3, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.130842
Keywords
Aza-Henry reaction; Chiral sulfinyl imines; 2-Pyrrolidones; Diazaspiro compounds; Intramolecular cyclizations
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Funding
- Ministerio de Economia y Competitividad of Spain (MINECO) [CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P]
- FEDER
- Generalitat Valenciana [PROM-ETEOII/2014/017]
- University of Alicante
- Ministere de l'Enseignement Superieur et de la Recherche Scientifique Algerienne [Direction de la Cooperation et des Echanges Interuniversitaires, Programme de Formation Residentielle l'Etranger au titre de l'annee universitaire 2016/2017: Programme Nation
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The reaction of N-tert-butanesulfinyl imines with ethyl 4-nitrobutanoate under basic conditions produced nitro amine derivatives. The resulting beta-nitroamine derivatives, isolated as a 1:1 mixture of epimers, were easily transformed into 5-(1-aminoalkyl)-2-pyrrolidones, upon reduction of the nitro group with concomitant gamma-lactam formation. On the other hand, selective removal of the sulfinyl group in the beta-nitroamine derivatives led to 5-nitropiperidin-2-ones in reasonable yields. From these compounds, and following a two-step process, involving conjugative addition to ethyl acrylate and final reduction of the nitro group, 1,7-diazaspiro[4.5]decane-2,8-diones were accessed in a highly stereoselective fashion. (C) 2019 Elsevier Ltd. All rights reserved.
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