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Journal articles
Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions
Abstract : We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.
Cited literature [44 references]
https://hal-pasteur.archives-ouvertes.fr/pasteur-01972149
Contributor : Yves Janin <>
Submitted on : Monday, January 7, 2019 - 3:20:36 PM
Last modification on : Monday, January 11, 2021 - 2:30:05 PM
Contributor : Yves Janin <>
Submitted on : Monday, January 7, 2019 - 3:20:36 PM
Last modification on : Monday, January 11, 2021 - 2:30:05 PM
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