Interrupted Polonovski Strategy for the Synthesis of Functionalized Amino Acids and Peptides

被引：2
作者：
Marty, Christine [1 ,2 ]
Allouche, Emmanuelle M. D. [1 ,2 ]
Waser, Jerome [1 ]
机构：
[1] Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland
[2] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Catalysis & Organ Synth, EPFL,SB,ISIC,LCSO, BCH 4306, CH-1015 Lausanne, Switzerland
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 02期
基金：
瑞士国家科学基金会;
关键词：
SELECTIVE CONVERSION; GLYCINE DERIVATIVES; IMINE SURROGATES; ONE-POT; ESTERS; ALKYLATION; GENERATION; RESIDUES;
D O I：
10.1021/acs.orglett.3c03603
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The alpha-functionalization of carbamate-protected hydroxylamine glycine derivatives, acting as imine surrogates via an interrupted Polonovski reaction, is described to access functionalized amino acid derivatives. The addition of C, N, O, and S nucleophiles was achieved in a one-pot procedure in 37% to 92% yield. This method could be extended to dipeptide derivatives for the functionalization of both the C-terminus and N-terminus.
引用
收藏
页码：456 / 460
页数：5
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