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M. Tissot, D. Müller, S. Belot, A. Alexakis,
“Enantioselective and Regiodivergent Copper-Catalyzed Conjugate Addition of Trialkylaluminium Reagents to Extended Nitro-Michael Acceptors”
Org. Lett. 2010, 12, 2770-2773.
The first highly enantioselective and regiodivergent conjugate addition of trialkylaluminium reagents to nitrodienes and nitroenynes is described. By a design of the substrate and a fine-tuning of the reaction conditions, it is possible to selectively form the 1,4- or 1,6-adduct. The same combination of catalyst, copper source, and a ferrocene-based phosphine ligand afforded enantioselectivities up to 95% and 91%, respectively.
DOI : 10.1021/ol100849j
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