An efficient synthesis of N^α-protected amino nitriles from N^α-protected amino acid amides employing Ph₃P, I₂ and NMM was described. Various amino acid amides, protected by Fmoc, Z and Boc were conveniently converted to nitriles in high yields. Side chain protected amino acid amides were well-tolerated and a good yield of products was obtained. The protocol serves as one of the mild, among a few available, methods for the racemization-free conversion of N^α-protected amino acid amides to corresponding nitriles with neither harsh condition nor catalyst.

Graphic Abstract

N^α-protected amino acid amides were efficiently transformed to N^α-protected amino acid nitriles employing I₂, PPh₃, and NMM under mild reaction conditions. Fmoc, Boc and Cbz-protected amino acid amides were converted into their corresponding nitriles groups. Side chain protected amino acid amides also underwent facile conversion to their corresponding nitriles with good yields.

中文翻译：

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阿普尔反应条件下手性α-酰胺脱水为手性α-腈

N的有效的合成^α -保护的氨基腈选自N ^α -保护的使用pH值氨基酰胺₃ P，I ₂和NMM被描述。受Fmoc，Z和Boc保护的各种氨基酸酰胺可方便地以高收率转化为腈。侧链保护的氨基酸酰胺具有良好的耐受性，并获得了良好的产物收率。该协议用作温和的一个，对于N的自由外消旋转换几个可用的，方法中^α -保护的氨基酸酰胺与既不苛刻的条件，也没有催化剂相应的腈。

图形摘要

Ñ ^α -保护的氨基酸酰胺被有效转化成N ^α采用我-保护氨基酸腈₂，PPH ₃，和NMM温和的反应条件下进行。Fmoc，Boc和Cbz保护的氨基酸酰胺被转化为相应的腈基。侧链保护的氨基酸酰胺也容易以良好的产率转化为其相应的腈。