Bifunctional squaramide catalyzed asymmetric synthesis of chiral α-mercaptosilanes

Abstract

Bifunctional squaramide-catalyzed nucleophilic addition of thiophenols to easily available β-silyl α,β-unsaturated carbonyl compounds has been successfully developed. A structurally diverse set of chiral α-mercaptosilanes was efficiently prepared in good to...

Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions

“…Metal-catalyzed reaction of various nucleophiles to β-silyl α,β-unsaturated carbonyl compounds were documented as one of the straightforward and atom-economic approaches for the facile synthesis of chiral organosilanes ( Scheme 1c –f) [ 30 – 33 ]. Recently, the aforementioned reaction under organocatalytic conditions has gained attention [ 34 – 36 ]. In this context, Huang, Fu and co-workers reported carbene-catalyzed enantioselective formal [4 + 2] annulation reactions of β-silyl enones with enals and with active acetic esters ( Scheme 1g ) for the preparation of chiral organosilanes [ 34 – 36 ].…”

“…Recently, the aforementioned reaction under organocatalytic conditions has gained attention [ 34 – 36 ]. In this context, Huang, Fu and co-workers reported carbene-catalyzed enantioselective formal [4 + 2] annulation reactions of β-silyl enones with enals and with active acetic esters ( Scheme 1g ) for the preparation of chiral organosilanes [ 34 – 36 ]. Very recently, during the final stage of our work, the same group disclosed an organocatalyzed conjugate addition of thiols to β-silyl enones for the synthesis of chiral α-mercaptosilanes ( Scheme 1g ) [ 36 ].…”