Radical-mediated opening of 2,3-epoxy alcohols using Cp2TiCl: stereoselective construction of quaternary chiral centers

Tushar Kanti Chakraborty; Rajarshi Samanta; Sanjib Das

doi:10.1021/jo0600961

Radical-mediated opening of 2,3-epoxy alcohols using Cp2TiCl: stereoselective construction of quaternary chiral centers

J Org Chem. 2006 Apr 14;71(8):3321-4. doi: 10.1021/jo0600961.

Authors

Tushar Kanti Chakraborty¹, Rajarshi Samanta, Sanjib Das

Affiliation

¹ Indian Institute of Chemical Technology, Hyderabad 500 007, India. chakraborty@iict.res.in

PMID: 16599641
DOI: 10.1021/jo0600961

Abstract

Radical-mediated opening of chiral 2,3-epoxy alcohols regioselectively at the 2-position using Cp2TiCl and trapping the intermediate radical with methyl acrylate and acrylonitrile led to the stereoselective formation of tetrasubstituted chiral centers.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alcohols / chemistry*
Free Radicals / chemistry
Molecular Structure
Stereoisomerism
Titanium / chemistry*

Substances

Alcohols
Free Radicals
Titanium