Synthesis and stereochemistry assignment of (3R,5R)- and (3S,5R)-4-benzyl-3-(3,4-dimethoxyphenyl)-5-phenyl-1,4-oxazin-2-ones

• Published in: Journal of molecular structure Vol. 1194; pp. 204 - 210
• Main Authors: Grajewska, Agnieszka, Rozwadowska, Maria D., Gzella, Andrzej
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.10.2019
• Subjects: 1,4-Oxazin-2-one; Configuration determination; Diastereoselective synthesis; NMR; Petasis reaction; X-ray; Configuration determination; Petasis reaction; Diastereoselective synthesis; NMR; X-ray; 1,4-Oxazin-2-one

The diastereoselective synthesis of 3,5-disubstituted 1,4-oxazin-2-ones, the valuable intermediates on the route to tetrahydroisoquinoline derivatives, was based on the Petasis reaction in which (R)-(−)-N-benzyl-2-phenylglycinol was used as the amine component. It was demonstrated that the configura...