Oxazolidine-2-thiones and thiazolidine-2-thiones as nucleophiles in intermolecular Michael additions.
Conjugate addition of thiazolidinethiones and oxazolidinethiones to N-crotonylthiazolidinethiones and -oxazolidinethiones was observed in the presence of excess triethylamine in dichloromethane. The addition takes place by the nitrogen of the heterocycle with high diastereoselectivity. It was observed that the stereoselective addition occurs on the anti-s-cis conformation of the N-enoyl sulfur-containing heterocycle.
Division of Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242, USA.
Laura
L
Munive
Veronica M
VM
Rivas
Aurelio
A
Ortiz
Horacio F
HF
Olivo
D015394:Molecular Structure; D013871:Thiones / Q000138:chemical synthesis* / Q000737:chemistry*
D013871:Thiones