5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids

被引：3

作者：

Habib, Asmaa ^{[1
]}

Garrido-Gonzalez, Jose J. ^{[1
]}

Sanchez-Santos, Estela ^{[1
]}

del Teso, Irene Boya ^{[1
]}

Sanz, Francisca ^{[3
]}

Alcazar, Victoria ^{[2
]}

de Arriba, Angel L. Fuentes ^{[1
]}

Moran, Joaquin R. ^{[1
]}

机构：

[1] Univ Salamanca, Organ Chem Dept, Salamanca 37008, Spain

[2] Univ Politecn Madrid, Environm & Ind Chem Engn Dept, Madrid 28006, Spain

[3] Univ Salamanca, X Ray Diffract Serv, Salamanca 37008, Spain

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 22期

关键词：

DERIVATIVES; LYSINE;

D O I：

10.1021/acs.orglett.3c01334

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of5-chloro-8-nitro-1-naphthoyl chloride and itsuse as a protective group for amines is described. Protection is carriedout with an auxiliary amine or under mild Schotten-Baumann conditionsin high yield (>86%), while deprotection can be achieved easilyundergentle reducing conditions due to the large steric tension betweenC-1 and C-8 naphthalene substituents. The reaction has been successfullytested in dipeptide synthesis and amino alcohols protection, and ithas proved selective for the epsilon-amine group of lysine.

引用

页码：4103 / 4107

页数：5

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