Abstract
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.
Original language | English |
---|---|
Pages (from-to) | 1283-1289 |
Journal | Journal of Organic Chemistry |
Volume | 68 |
Issue number | 4 |
DOIs | |
Publication status | Published - 21 Feb 2003 |