Organic Letters
Organic Letters
5 years ago

Chiral Cyclic Ligand-Enabled Iridium-Catalyzed Asymmetric Arylation of Unactivated Racemic Allylic Alcohols with Anilines

Chiral Cyclic Ligand-Enabled Iridium-Catalyzed Asymmetric Arylation of Unactivated Racemic Allylic Alcohols with Anilines
Haijun Yang, Hua Fu, Fei Peng, Hua Tian, Pengxiang Zhang
A highly enantioselective arylation of unactivated racemic secondary allylic alcohols with aniline derivatives has been developed. The transformation was enabled by an iridium–chiral cyclic phosphoramidite complex in the presence of boron trifluoride diethyl etherate as the promoter, and the reactivity and enantioselectivity of the substrates were tuned by the variation of our newly developed chiral cyclic phosphoramidite ligands together with temperature and solvents. The method shows advantages including use of the readily available starting materials, an operationally convenient protocol, full regioselectivity and excellent enantioselectivity, and tolerance of many functional groups with water as the only byproduct.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01631

DOI: 10.1021/acs.orglett.7b01631

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