jo6b00643_si_001.pdf (2.7 MB)
Formal [3 + 2] Reaction of α,α-Diaryl Allylic Alcohols with sec-Alcohols: Proceeding with Sequential Radical Addition/Migration toward 2,3-Dihydrofurans Bearing Quaternary Carbon Centers
journal contribution
posted on 2016-05-02, 00:00 authored by Weiming Hu, Song Sun, Jiang ChengAn unprecedented
TBHP-promoted formal [3 + 2] annulation of sec-alcohols
with α,α-diaryl allylic alcohols
has been developed, leading to 2,3-dihydrofurans in moderate to excellent
yields with good functional group tolerance. This procedure involves
sequential radical addition, 1,2-aryl migration, and a dehydration
process, where the migration of aryl with lower electron density is
favored. Notably, cyclic reactions with sec-alcohols
also ran smoothly, providing a novel method to access oxaspiro compounds.