Derivatization of Amino Acids and Peptides via Photoredox-Mediated Conjugate Addition

被引:40
|
作者
Zhang, Olivia [1 ]
Schubert, Jeffrey W. [1 ]
机构
[1] Merck & Co Inc, Dept Discovery Chem, West Point, PA 19486 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 09期
关键词
DERIVATIVES; ROUTE;
D O I
10.1021/acs.joc.0c00635
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unnatural amino acids are key building blocks in therapeutically relevant peptides. Thus, the development of novel methods to increase the structural diversity of the unnatural amino acid pool is needed. Herein, a photoredox-mediated decarboxylative radical conjugate addition to dehydroalanine derivatives is disclosed. Mild, robust, and general conditions were identified and applied to the diastereoselective synthesis of unnatural amino acids and the late-stage derivatization of a tripeptide.
引用
收藏
页码:6225 / 6232
页数:8
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