Organic Chemistry Portal

Abstracts

Search:

An Efficient and Solvent-Free Synthesis of Mixed Ortho Esters

Kelly L. Cosgrove, Ross P. McGeary*

*School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, Queensland 4072, Australia, Email: r.mcgearyuq.edu.au

K. L. Cosgrove, R. P. McGeary, Synlett, 2008, 2425-2428.

DOI: 10.1055/s-2008-1078215 (free Supporting Information)


Abstract

Primary, secondary and electron-deficient tertiary alcohols react rapidly with ketene dimethyl acetal to form mixed ortho esters, without catalysts and under solvent-free conditions. 1,2-Diols yield bis(mixed ortho esters), rather than cyclic ortho esters.


see article for more examples



A Convenient Triisobutylaluminium (TIBAL)-Promoted Johnson-Claisen Approach to γ,δ-Unsaturated Alcohols

K. L. Cosgrove, R. P. McGeary, Synlett, 2009, 1749-1752.


Key Words

ortho esters, ketene dimethyl acetal, alcohols, cyanohydrins, 1,2-diols


ID: J60-Y2008-2730