ol5005752_si_001.pdf (30.91 MB)
Domino Asymmetric Conjugate Addition–Conjugate Addition
journal contribution
posted on 2014-04-04, 00:00 authored by Nicolas Germain, Doriane Schlaefli, Mathieu Chellat, Stéphane Rosset, Alexandre AlexakisEnantioenriched 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.