Stereoselective Activation of Small Molecules by a Stable Chiral Silene.

ABSTRACT: The reaction of the dilithium salt of the enantiopure (S)-BINOL (1,1'-bi-2-naphthol) with two equivalents of the amidinate-stabilized chlorosilylene [L^Ph SiCl] (L^Ph =PhC(NtBu)₂ ) led to the formation of the first example of a chiral cyclic silene species comprising an (S)-BINOL ligand. The reactivity of the Si=C bond was investigated by reaction with elemental sulfur, CO₂ and HCl. The reaction with S₈ led to a Si=C bond cleavage and concomitantly to a ring-opened product with imine and silanethione functional groups. The reaction with CO₂ resulted in the cleavage of the CO₂ molecule into a carbonyl group and an isolated O atom, while a new stereocenter is formed in a highly selective manner. According to DFT calcu

SUBMITTER: Sun X 

PROVIDER: S-EPMC9805157 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature