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

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

Organic letters (2012-04-14)
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
PMID22497425
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.