Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions
2018 ◽
Vol 14
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pp. 2846-2852
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Keyword(s):
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.
2008 ◽
Vol 49
(15)
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pp. 2432-2434
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2002 ◽
Vol 67
(11)
◽
pp. 1635-1646
2011 ◽
Vol 133
(42)
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pp. 16970-16976
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Keyword(s):
1994 ◽
Vol 67
(1)
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pp. 271-273
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2005 ◽
Vol 2005
(11)
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pp. 733-735
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Keyword(s):