Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Enantioselective Conjugate Addition of 2-Acetyl Azaarenes to β,β-Disubstituted Nitroalkene for the Construction of All-Carbon Quaternary Stereocenters

Enantioselective Conjugate Addition of 2-Acetyl Azaarenes to β,β-Disubstituted Nitroalkene for the Construction of All-Carbon Quaternary Stereocenters
Lin-gang Wu, Zhaohai Qin, Lei Xie, Bin Fu, Zhenhua Zhang, Hongli Ma
The first highly enantioselective conjugate addition of 2-acetyl azaarenes to α-substituted-β-nitroacrylates was successfully realized under mild conditions by a Ni(II)-bisoxazoline complex, providing the desired adducts bearing an all-carbon quaternary stereocenter in high yield with excellent enantioselectivity. The products obtained in this system could be readily converted into optically active β2,2-amino esters, succinates, lactones, and lactams.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01014

DOI: 10.1021/acs.joc.7b01014

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