Stereoselective, Ruthenium-Photocatalyzed Synthesis of 1,2-Diaminotruxinic Bis-amino Acids from 4-Arylidene-5(4H)-oxazolones.

ABSTRACT: The irradiation of (Z)-2-phenyl-4-aryliden-5(4H)-oxazolones 1 in deoxygenated CH₂Cl₂ at 25 °C with blue light (465 nm) in the presence of [Ru(bpy)₃](BF₄)₂ (5% mole ratio) as a triplet photocatalyst promotes the [2+2] photocycloaddition of the C═C bonds of the 4-arylidene moiety, thus allowing the completely regio- and stereoselective formation of cyclobutane-bis(oxazolone)s 2 as single stereoisomers. Cyclobutanes 2 have been unambiguously characterized as the μ-isomers and contain two E-oxazolones coupled in an anti-head-to-head form. The use of continuous-flow techniques in microreactors allows the synthesis of cyclobutanes 2 in only 60 min, compared with the 24-48 h required in

SUBMITTER: Sierra S 

PROVIDER: S-EPMC8902759 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature