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金(III)催化邻氨基苯甲酸与N-烯丙基酰胺的化学选择性环化反应合成3-氮杂双环[3.1.0]己烷-2-亚胺

Gold(iii)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines.

作者信息

Song Lina, Tian Xianhai, Rudolph Matthias, Rominger Frank, Hashmi A Stephen K

机构信息

Institute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

出版信息

Chem Commun (Camb). 2019 Aug 7;55(61):9007-9010. doi: 10.1039/c9cc04027g. Epub 2019 Jul 10.

DOI:10.1039/c9cc04027g
PMID:31290870
Abstract

We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the gram scale, tolerates electron-rich and electron-deficient anthranils as well as a diverse set of functionalized ynamides (aryl- and alkyl-substituted terminal).

摘要

我们在此报告了在温和条件下金(III)催化邻氨基苯甲腈与N-烯丙基酰胺的选择性环化反应。通过捕获原位生成的α-亚氨基金卡宾,以高合成效率得到了3-氮杂双环[3.1.0]己烷-2-亚胺。该反应可以进行克级规模的操作,对富电子和缺电子的邻氨基苯甲腈以及多种官能化的炔酰胺(芳基和烷基取代的端基)均具有耐受性。

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