Synthesis of α-amino acid precursors directly from aldehydes using masked acyl cyanide reagents and N,O-dialkylated hydroxylamines
Synthesis of α-amino acid precursors directly from aldehydes using masked acyl cyanide reagents and N,O-dialkylated hydroxylamines
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DOI：
10.1021/jo0607515
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发表时间：
2006-08-04
影响因子：
3.6
通讯作者：
Shibuya, Masayuki
中科院分区：
文献类型：
--
作者：
Nemoto, Hisao;Ma, Rujian;Shibuya, Masayuki
研究了一种利用N，O-二烷基羟胺和掩蔽的酰基氰（MAC）试剂直接从相应的醛合成α-氨基酸前体的合成方法。一锅法反应可以在温和条件下进行，并且不需要单独的亚氨基物质纯化步骤。以Abiko-Masamune的三环1，2-恶唑烷为手性助剂，合成了光学纯的（+）-4-甲基苯甘氨酸及其衍生物。
A synthetic methodology for the synthesis of alpha-amino acid precursors directly from the corresponding aldehydes using N,O-dialkylated hydroxylamines and masked acyl cyanide (MAC) reagents was developed. The one-pot reaction can be carried out under mild conditions and without a separate purification step of the imino species. The method was applied to the synthesis of optically pure (+)-4-methylphenylglycine and the derivatives by using an Abiko-Masamune's tricyclic 1,2-oxazolidine as the chiral auxiliary.