Organic Letters 2012-05-04

Efficient chiral monophosphorus ligands for asymmetric Suzuki-Miyaura coupling reactions.

Wenjun Tang, Nitinchandra D Patel, Guangqing Xu, Xiaobing Xu, Jolaine Savoie, Shengli Ma, Ming-Hong Hao, Santosh Keshipeddy, Andrew G Capacci, Xudong Wei, Yongda Zhang, Joe J Gao, Wenjie Li, Sonia Rodriguez, Bruce Z Lu, Nathan K Yee, Chris H Senanayake

Index: Org. Lett. 9th ed., 14 , 2258-2261, (2012)

Full Text: HTML

Abstract

A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki-Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety in these chiral biaryl products allows facile derivatization for further synthetic applications. A computational study has revealed that a π-π interaction between the two coupling partners can enhance the enantioselectivity of the coupling reaction.