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由ω-氨基-H-次膦酸酯合成P，N-杂环：构象受限的α-氨基酸类似物

Synthesis of P,N-heterocycles from omega-amino-H-phosphinates: conformationally restricted alpha-amino acid analogs.

作者信息

Queffelec Clémence, Ribière Patrice, Montchamp Jean-Luc

机构信息

Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, USA.

出版信息

J Org Chem. 2008 Nov 21;73(22):8987-91. doi: 10.1021/jo801768y. Epub 2008 Oct 15.

DOI:10.1021/jo801768y
PMID:18855477
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2670240/
Abstract

P,N-heterocycles (3-hydroxy-1,3-azaphospholane and 3-hydroxy-1,3-azaphosphorinane-3-oxide) are synthesized in moderate yield from readily available omega-amino-H-phosphinates and aldehydes or ketones via an intramolecular Kabachnik-Fields reaction. The products are conformationally restricted phosphinic analogs of alpha-amino acids. The multigram-scale syntheses of the H2N(CH2)(n)PO2H2 phosphinic precursors (n = 1, 2, 3) and some derivatives are also described.

摘要

通过分子内的卡巴奇尼克-菲尔德反应，由容易获得的ω-氨基-H-次膦酸酯与醛或酮以中等产率合成了P，N-杂环化合物（3-羟基-1,3-氮杂磷环戊烷和3-羟基-1,3-氮杂磷环己烷-3-氧化物）。产物是α-氨基酸的构象受限的次膦酸类似物。还描述了H2N(CH2)(n)PO2H2次膦酸前体（n = 1, 2, 3）及其一些衍生物的多克规模合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/b794dc8909fd/nihms86437f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/806ceba792f4/nihms86437f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/6949116945f3/nihms86437f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/e7f12b39dfd4/nihms86437f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/b794dc8909fd/nihms86437f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/806ceba792f4/nihms86437f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/6949116945f3/nihms86437f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/e7f12b39dfd4/nihms86437f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/649e/2670240/b794dc8909fd/nihms86437f4.jpg

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本文引用的文献

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