Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO

The reaction of the chiral nitrone MiPNO (2-isopropyl-2,3-dimethyl-1-oxy-2,3-dihydro-imidazol-4-one) with Grignard reagents is totally diastereoselective. Using simple and functionalized arylmagnesium reagents, enantiopure hydroxylamines were obtained in fair to good yields, which in turn could be e...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2011-06, Vol.22 (12), p.1274-1281
Main Authors: Thiverny, Maryse, Farran, Daniel, Philouze, Christian, Blandin, Véronique, Chavant, Pierre Y.
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:The reaction of the chiral nitrone MiPNO (2-isopropyl-2,3-dimethyl-1-oxy-2,3-dihydro-imidazol-4-one) with Grignard reagents is totally diastereoselective. Using simple and functionalized arylmagnesium reagents, enantiopure hydroxylamines were obtained in fair to good yields, which in turn could be easily transformed into new chiral ketonitrones. The preparation of enantiopure l-phenylglycine derivatives is also described.
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/j.tetasy.2011.07.022