Hydroxyalkylation of alpha-C-H bonds of tetrahydrofuran with aldehydes in the presence of triethylborane and tert-butyl hydroperoxide

Takehiko Yoshimitsu; Yoshimasa Arano; Hiroto Nagaoka

doi:10.1021/jo020590e

Hydroxyalkylation of alpha-C-H bonds of tetrahydrofuran with aldehydes in the presence of triethylborane and tert-butyl hydroperoxide

J Org Chem. 2003 Jan 24;68(2):625-7. doi: 10.1021/jo020590e.

Authors

Takehiko Yoshimitsu¹, Yoshimasa Arano, Hiroto Nagaoka

Affiliation

¹ Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan. takey@my-pharm.ac.jp

PMID: 12530897
DOI: 10.1021/jo020590e

Abstract

The alpha-hydroxyalkylation of tetrahydrofuran with aldehydes via radical C-H abstraction was conducted using triethylborane in the presence of tert-butyl hydroperoxide. This study presents a rare instance of direct intermolecular radical addition of unactivated cyclic ether to aldehydes.