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Publication 334
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N. Germain, D. Schlaefli, M. Chellat, S. Rosset, A. Alexakis,
“Domino Asymmetric Conjugate Addition-Conjugate Addition”
Org. Lett. 2014, 16, 2006-2009.
Enantioenriched Al-, Mg-, and Zn-enolates undergo electrophilic trapping by nitroolefins and vinylsulfones to afford 1,4-diketones and 2-(bis(phenylsulfonyl)ethyl)ketones in good yield and excellent diastereoselectivity. A one-pot preparation of indenes and enantiopure syntheses of tetrahydrobenzofurans, tetrahydrobenzopyrroles, and azulenes are disclosed. A site-selective two-step sequence of three conjugate additions is also demonstrated.
DOI : 10.1021/ol5005752
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