Enantioconvergent and Regioselective Synthesis of Allenylsilanes by Nickel-Catalyzed C(sp2)-C(sp3) Cross-Coupling Starting from Racemic a-Silylated Propargylic Bromides

A direct synthesis of enantioenriched allenylsilanes from racemic a-silylated propargylic bromides by an enantioconvergent nickel-catalyzed cross-coupling is reported. The high regioselectivity is governed by the bulky silyl group, and the C(sp(2))-C(sp(3)) bond formation occurs exclusively at the y-position of the propargyl electrophile. The level of enantioselection induced by a chiral Pybox ligand is moderate.

Automated summary

This study reports a direct synthesis of enantioenriched allenylsilanes from racemic a-silylated propargylic bromides through an enantioconvergent nickel-catalyzed cross-coupling. The regioselectivity is controlled by the bulky silyl group, and the bond formation occurs exclusively at the y-position of the propargyl electrophile. The level of enantioselection induced by a chiral Pybox ligand is moderate.