386744-36-1Relevant academic research and scientific papers
Photochemical [2 + 2] cycloaddition of acetylene to chiral 2(5H)-furanones
Alibes, Ramon,De March, Pedro,Figueredo, Marta,Font, Josep,Fu, Xiaolin,Racamonde, Marta,Alvarez-Larena, Angel,Piniella, Juan F.
, p. 1283 - 1289 (2003)
The [2 + 2] photocycloaddition of acetylene to chiral 2(5H)-furanones was investigated. The influence on the chemical yield and facial diastereoselectivity of the substituent at the stereogenic center and also the effect of a 4-methyl group were evaluated. A mechanistic proposal based on a simple theoretical conformational analysis is presented. Using a C2-symmetric bis(lactone) as the substrate, a diastereomeric excess higher than 98% was found.
