Remarkable enhancement of enantioselectivity in the asymmetric conjugate addition of dimethylzinc to (Z)-nitroalkenes with a catalytic [(MeCN)₄Cu]PF₆-Hoveyda ligand complex.

Angewandte Chemie (International ed. in English) 2014 Nov 3

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An enantioselective copper-catalyzed asymmetric conjugate addition of Me2Zn to (Z)-nitroalkenes led to the formation of all-carbon quaternary stereogenic centers with high stereoselectivity. The key features of the new method are the unprecedented use of [(MeCN)4Cu]PF6 in conjunction with the Hoveyda ligand L1 and the use of (Z)-nitroalkene substrates so that undesired nitroalkene isomerization is minimized and enantioselectivity is enhanced dramatically. We also describe a novel, practical, and highly (Z)-selective nitroalkene synthesis. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Xingzhong Zeng, Joe J Gao, Jinhua J Song, Shengli Ma, Jean-Nicolas Desrosiers, Jason A Mulder, Sonia Rodriguez, Melissa A Herbage, Nizar Haddad, Bo Qu, Keith R Fandrick, Nelu Grinberg, Heewon Lee, Xudong Wei, Nathan K Yee, Chris H Senanayake. Remarkable enhancement of enantioselectivity in the asymmetric conjugate addition of dimethylzinc to (Z)-nitroalkenes with a catalytic [(MeCN)₄Cu]PF₆-Hoveyda ligand complex. Angewandte Chemie (International ed. in English). 2014 Nov 3;53(45):12153-7