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使用硝基乙酸乙酯并通过缩合或环加成反应合成非天然α-氨基酸酯。

Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions.

作者信息

Gagnot Glwadys, Hervin Vincent, Coutant Eloi P, Desmons Sarah, Baatallah Racha, Monnot Victor, Janin Yves L

机构信息

Unité de Chimie et Biocatalyse, Département de Biologie Structurale et Chimie, Institut Pasteur, 28 rue du Dr. Roux, 75724 Paris Cedex 15, France.

Unité Mixte de Recherche 3523, Centre National de la Recherche Scientifique, 28 rue du Dr. Roux, 75724 Paris Cedex 15, France.

出版信息

Beilstein J Org Chem. 2018 Nov 15;14:2846-2852. doi: 10.3762/bjoc.14.263. eCollection 2018.

DOI:10.3762/bjoc.14.263
PMID:30498535
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6244114/
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 (NaBH 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.

摘要

我们在此报告使用硝基乙酸乙酯作为甘氨酸模板来制备α-氨基酯。这始于对其与各种芳基缩醛缩合生成3-芳基-2-硝基丙烯酸乙酯的研究，随后通过还原（先用硼氢化钠，然后用锌/盐酸）得到α-氨基酯。我们探索了该方法的适用范围以及用芳基酰基缩醛替代的另一种方法。我们还关注了各种[2 + 3]环加成反应，其中一种反应生成了螺缩醛，该反应导致了不需要的5-（苯甲酰胺基甲基）异恶唑-3-羧酸乙酯。我们还探索了使用硝酸铈铵将硝基乙酸乙酯加成到5-亚甲基-4,5-二氢恶唑上的反应，并利用金（I）化学实现了其他含恶唑的α-氨基酯的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/a0bb1ad9fe35/Beilstein_J_Org_Chem-14-2846-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/34614a3742b5/Beilstein_J_Org_Chem-14-2846-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/8bc3d5709625/Beilstein_J_Org_Chem-14-2846-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/df72b51c2234/Beilstein_J_Org_Chem-14-2846-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/b4566cd5a8ad/Beilstein_J_Org_Chem-14-2846-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/a0bb1ad9fe35/Beilstein_J_Org_Chem-14-2846-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/34614a3742b5/Beilstein_J_Org_Chem-14-2846-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/8bc3d5709625/Beilstein_J_Org_Chem-14-2846-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/df72b51c2234/Beilstein_J_Org_Chem-14-2846-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/b4566cd5a8ad/Beilstein_J_Org_Chem-14-2846-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3087/6244114/a0bb1ad9fe35/Beilstein_J_Org_Chem-14-2846-g006.jpg

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