1,8-二氮杂环[5.4.0]十一烷-7-烯介导的烯酰胺氢烷基化合成β-氨基酯。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-02-28 Epub Date: 2025-02-13 DOI:10.1021/acs.joc.4c02968

Xiao Yang, Junyi Wang, Haoran Liang, Rui Sun

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引用次数: 0

摘要

建立了一种1,8-重氮双环[5.4.0]十一烷-7-烯（DBU）介导的烯酰胺与丙二酸二酯/β-羰基酯的氢烷基化反应，该反应无金属介入，反应条件温和，官能团耐受性好。该方案使各种β-氨基酯的快速制备。初步的机制研究，包括控制实验和关键中间体的捕获实验，已经证实了dbu介导的氢烷基化途径。

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Synthesize of β-Amino Esters from Enamides via 1,8-Diazabicyclo[5.4.0]undecane-7-ene-Mediated Hydroalkylation.

A 1,8-diazabicyclo[5.4.0]undecane-7-ene (DBU)-mediated hydroalkylation of enamides with malonic acid diesters/β-carbonyl esters has been established, featuring no metal involvement, mild reaction conditions, and good functional group tolerance. The protocol enables the expedited preparation of a variety of β-amino esters. Preliminary mechanistic investigations, encompassing control experiments and capture experiments of key intermediates, have substantiated the proposed DBU-mediated hydroalkylation pathway.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.