Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins
Oleg I. Afanasyev, Fedor S. Kliuev, Alexey A. Tsygankov, Yulia V. Nelyubina, Evgenii Gutsul, Valentin V. Novikov and Denis Chusov*
*A.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova St. 28, Moscow 119991, Russian Federation,
Email: denis.chusov
gmail.com
O. I. Afanasyev, F. S. Kliuev, A. A. Tsygankov, Y. V. Nelyubina, E. Gutsul, V. V. Novikov, D. Chusov, J. Org. Chem., 2022, 87, 12182-12195.
DOI: 10.1021/acs.joc.2c01339
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Abstract
Bromide-nickel diimine complexes catalyze asymmetric Michael addition in low yields and ee, but activation with fluoride ions leads to a significant improvement in catalyst performance. The developed approach was applied to the preparation of several enantioenriched GABA analogues.
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proposed mechanism
Key Words
activated methylene compounds, nitro compounds
ID: J42-Y2022
