Domino Asymmetric Conjugate Addition–Conjugate
Addition
Nicolas Germain
Doriane Schlaefli
Mathieu Chellat
Stéphane Rosset
Alexandre Alexakis
10.1021/ol5005752.s001
https://acs.figshare.com/articles/journal_contribution/Domino_Asymmetric_Conjugate_Addition_Conjugate_Addition/2309242
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.
2014-04-04 00:00:00
sequence
enantiopure syntheses
domino
diastereoselectivity
Asymmetric
electrophilic
azulene
diketone
Mg
bi
tetra
AdditionEnantioenriched
vinylsulfone
Al
conjugate additions
preparation
indene
Conjugate
nitroolefin