Carbon-silicon-switch effect in enantioselective construction of silicon-stereogenic center from silacyclohexadienones.

ABSTRACT: Carbon-silicon-switch strategy, replacing one specific carbon atom in organic molecules with a silicon, has garnered significant interest for developing new functional molecules. However, the influence of a reaction regarding its selectivity and reactivity by carbon-silicon-switch strategy has far less been investigated. Here we discover an unusual carbon-silicon-switch effect in the enantioselective construction of silicon-stereogenic center. It is found that there has been a significant change in the desymmetrization reaction of silacyclohexadienones using asymmetric conjugate addition or oxidative Heck reaction with aryl/alkyl nucleophiles when compared with their carbon analogues cyclohexadienones. Specifically, the carbon-silicon-switch leads to a reversal in enantioselectivity with a

SUBMITTER: Yan Y 

PROVIDER: S-EPMC11568255 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature