Divergent Synthesis of <i>gem</i>-Difluorinated Oxa-Spirocyclohexadienones by One-Pot Sequential Reactions of <i>p</i>-Hydroxybenzyl Alcohols with Difluoroenoxysilanes
Haijian Wu, Hong Peng, Wenxue Xi, Jinshan Li
Abstract
A new efficient formal [2 + 3] cyclization of p-hydroxybenzyl alcohols with difluoroenoxysilanes has been established. This convenient one-pot sequential procedure enables the divergent construction of highly functionalized gem-difluorinated oxa-spirocyclohexadienones under mild conditions. As opposed to the common C1 synthons in previous studies, difluoroenoxysilanes acted as new 3-atom (CCO) synthons for the first time here. The AcOH and H2O generated in the reaction are critical for the reactions to proceed smoothly.
Topics & Concepts
SynthonChemistryCombinatorial chemistryFormal synthesisDivergent synthesisAtom (system on chip)Reaction conditionsStereochemistryOrganic chemistryCatalysisParallel computingComputer scienceFluorine in Organic ChemistryOxidative Organic Chemistry ReactionsAsymmetric Synthesis and Catalysis