β，γ-炔基-α-酮胺酯与1,3-二羰基的区域选择性[3 + 2]环化：高功能化二氢呋喃的合成。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-02-14 Epub Date: 2025-01-30 DOI:10.1021/acs.joc.4c02393

Ting Zhao, Xuecai Tan, Ping Tang, Lin Xie, Yaowen Qin, Haiyue Cai, Huishan Zhao, Qin Huang, Sasa Wang

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引用次数: 0

摘要

揭示了β，γ-炔基-α-酮胺酯与1,3-二羰基的区域选择性[3 + 2]环。在不使用碱的情况下，获得了一系列带有外环双键和季碳中心的z选择性二氢呋喃。通过对照实验和氘标记实验探讨了反应机理。催化剂和无碱的亲核加成突出了转化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Regioselective [3 + 2] Annulation of β,γ-Alkynyl-α-ketimino Esters with 1,3-Dicarbonyls: The Synthesis of Highly Functionalized Dihydrofurans.

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Regioselective [3 + 2] Annulation of β,γ-Alkynyl-α-ketimino Esters with 1,3-Dicarbonyls: The Synthesis of Highly Functionalized Dihydrofurans.

A regioselective [3 + 2] annulation of β,γ-alkynyl-α-ketimino esters with 1,3-dicarbonyls is disclosed. A series of Z-selective dihydrofurans bearing an exocyclic double bond and a quaternary carbon center are accessed without the usage of base. Control and deuterium-labeling experiments have been investigated to probe into the reaction mechanism. The catalyst and base-free nucleophilic addition highlights the transformation.

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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.