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

页码：456 / 460

页数：5

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