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通过原位生成唑鎓烯醇盐实现二氢喹诺酮的对映选择性环化反应。

Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

作者信息

Lee Anna, Younai Ashkaan, Price Christopher K, Izquierdo Javier, Mishra Rama K, Scheidt Karl A

机构信息

Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University , Silverman Hall, Evanston, Illinois 60208, United States.

出版信息

J Am Chem Soc. 2014 Jul 30;136(30):10589-92. doi: 10.1021/ja505880r. Epub 2014 Jul 15.

Abstract

A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.

摘要

已开发出一种用于合成二氢喹诺酮的收敛性、催化不对称形式的[4 + 2]环化反应。羧酸可通过原位活化策略用作NHC烯醇盐的前体。在用于生成NHC的碱性条件下同时生成活性氮杂邻醌甲基化物,从而导致双重活化方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9df5/4120988/2fcc6d433520/ja-2014-05880r_0010.jpg

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