铜催化肟乙酸酯与α-氨基酸酯衍生物的环化反应：3-磺酰胺基/亚氨基-4-吡咯啉-2-酮的合成

Copper-Catalyzed Annulation of Oxime Acetates with α-Amino Acid Ester Derivatives: Synthesis of 3-Sulfonamido/Imino 4-Pyrrolin-2-ones.

作者信息

Miao Chun-Bao, Zheng An-Qi, Zhou Li-Jin, Lyu Xinyu, Yang Hai-Tao

机构信息

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China.

出版信息

Org Lett. 2020 May 1;22(9):3381-3385. doi: 10.1021/acs.orglett.0c00870. Epub 2020 Apr 13.

DOI:10.1021/acs.orglett.0c00870

PMID:32282212

Abstract

A copper-catalyzed annulation of oxime acetates and α-amino acid ester derivatives for the easy preparation of 4-pyrrolin-2-ones bearing a 3-amino group has been developed. This process features the oxidation of amines with oxime esters as the internal oxidant to produce the active 1,3-dinucleophilic and 1,2-dielectrophilic species concurrently. The subsequent nucleophilic cyclization realizes the efficient construction of 4-pyrrolin-2-one derivatives.

摘要

已开发出一种铜催化的肟乙酸酯与α-氨基酸酯衍生物的环化反应，用于简便制备带有3-氨基的4-吡咯啉-2-酮。该过程的特点是以肟酯作为内氧化剂氧化胺，同时生成活性的1,3-双亲核和亲双电物种。随后的亲核环化实现了4-吡咯啉-2-酮衍生物的高效构建。