Divergent Synthesis of gem-Difluorinated Oxa-Spirocyclohexadienones by One-Pot Sequential Reactions of p-Hydroxybenzyl Alcohols with Difluoroenoxysilanes

Haijian Wu; Peng Hong; Wenxue Xi; Jinshan Li

doi:10.1021/acs.orglett.2c00550

Divergent Synthesis of gem-Difluorinated Oxa-Spirocyclohexadienones by One-Pot Sequential Reactions of p-Hydroxybenzyl Alcohols with Difluoroenoxysilanes

Org Lett. 2022 Apr 8;24(13):2488-2493. doi: 10.1021/acs.orglett.2c00550. Epub 2022 Mar 28.

Authors

Haijian Wu¹, Peng Hong¹, Wenxue Xi¹, Jinshan Li¹

Affiliation

¹ Advanced Research Institute and Department of Chemistry, Taizhou University, Jiaojiang, Zhejiang 318000, P. R. China.

PMID: 35344353
DOI: 10.1021/acs.orglett.2c00550

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.