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
收藏
页码：4103 / 4107
页数：5
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