A class of readily available optically pure 7,7′-disubstituted BINAPs for asymmetric catalysis
作者:Wei-Cheng Yuan、Lin-Feng Cun、Ai-Qiao Mi、Yao-Zhong Jiang、Liu-Zhu Gong
DOI:10.1016/j.tet.2009.03.066
日期:2009.5
A class of optically pure 7,7'-disubstituted BINAPs have been prepared starting with a catalytic asymmetric oxidative Coupling reaction. A general, concise, and straightforward synthetic procedure has been established, and is suitable for all optically pure 7,7'-disubstituted BINAPs 1a-h, regardless of the substituents' structure in the 7,7'-positions. The catalytic potential of this class of ligands has been investigated in the highly enantioselective Rh-catalyzed 1,4-addition of aryl boronic acids to enones (up to 99.8% ee), and Ru-catalyzed asymmetric hydrogenation of simple aromatic ketones (up to S/C=100,000, up to 98% ee) and beta-ketoesters (up to S/C= 10,000, up to 99.8% ee), respectively. (C) 2009 Elsevier Ltd. All rights reserved.