title: Photochemical [2 + 2] cycloaddition of acetylene to chiral 2(5H)-furanones.
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 C(2)-symmetric bis(lactone) as the substrate, a diastereomeric excess higher than 98% was found.
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
authors.forename: Ramon
authors.initials: R
authors.lastname: Alibés
authors.forename: Pedro
authors.initials: P
authors.lastname: de March
authors.forename: Marta
authors.initials: M
authors.lastname: Figueredo
authors.forename: Josep
authors.initials: J
authors.lastname: Font
authors.forename: Xiaolin
authors.initials: X
authors.lastname: Fu
authors.forename: Marta
authors.initials: M
authors.lastname: Racamonde
authors.forename: Angel
authors.initials: A
authors.lastname: Alvarez-Larena
authors.forename: Juan F
authors.initials: JF
authors.lastname: Piniella