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Org Lett. 2012 May 4;14(9):2258-61. doi: 10.1021/ol300659d. Epub 2012 Apr 12.

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

Author information

1
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China. tangwenjun@sioc.ac.cn

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.

PMID:
22497425
DOI:
10.1021/ol300659d
[Indexed for MEDLINE]

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