The Kulinkovich Reaction on Lactones. A Convenient Approach to Functionalized Cyclopropanols
Annamaria Esposito and Maurizio Taddei*
*Dipartimento Farmaco Chimico Tecnologico, Polo Scientifico San Miniato, Via
Aldo Moro 2, 53100 Siena, Italy, Email: taddei.m
unisi.it
A. Esposito, M. Taddei, J. Org. Chem., 2000, 65, 9245-9248.
DOI: 10.1021/jo0011944
Abstract
The Kulinkovich reaction can be carried out successfully on lactones or THP-protected hydroxy esters to give cyclopropyl diols.
see article for more examples
comparison of the proposed mechanism of the Kulinkovich reaction on esters with a possible mechanism on lactones
Details
The document discusses the Kulinkovich reaction applied to lactones as a method to synthesize functionalized cyclopropanols. Cyclopropane-containing molecules are significant due to their biological properties and synthetic utility, particularly in antiviral and antitumor agents. The authors aimed to create new structures with a cyclopropane, an OH group, and a nucleobase. They proposed a synthetic route starting from hydroxy acids, involving multiple steps, but found lactones to be more efficient substrates. The modified Kulinkovich reaction on β-, γ-, and δ-lactones yielded cyclopropyl diols in good yields. The reaction required a THF/Et2O solvent mixture to avoid byproducts. The diols were selectively functionalized, and the methanesulfonyl group was used for activation and protection. The authors successfully synthesized nucleoside analogues and tested them for antiviral properties. The study demonstrated the effectiveness of the Kulinkovich reaction on lactones and THP-protected hydroxy esters, providing a convenient approach to functionalized cyclopropanols. The work was supported by the University of Sassari, and the authors acknowledged technical assistance and provided supporting spectral data online.
Key Words
Kulinkovich Reaction, Cyclopronanols
ID: J42-Y2000-630
