NDLI: Indium-mediated diastereoselective allylation of N-tert-butanesulfinyl imines derived from α-ketoesters

Content Provider	Semantic Scholar
Author	Maciá, Edgar Foubelo, Francisco Yus, Miguel
Copyright Year	2016
Abstract	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 C N 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.
Starting Page	6001
Ending Page	6010
Page Count	10
File Format	PDF HTM / HTML
DOI	10.1016/j.tet.2016.07.020
Volume Number	72
Alternate Webpage(s)	https://rua.ua.es/dspace/bitstream/10045/58079/2/2016_Macia_etal_Tetrahedron_accepted.pdf
Alternate Webpage(s)	https://doi.org/10.1016/j.tet.2016.07.020
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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