Abstract
| - A variety of prop-2-ynylamides have been carbonylated under oxidative conditions to give oxazolines,oxazolines with chelating groups, and bisoxazolines bearing an (alkoxycarbonyl)methylene chainat the 5 position in good yields. The cyclization−alkoxycarbonylation process was carried out inalcoholic media at 50−70 °C and under 24 bar pressure of 3:1 carbon monoxide/air in the presenceof catalytic amounts of 10% Pd/C or PdI2 in conjunction with KI. Cyclization occurred by anti attackof an oxygen function on the palladium-coordinated triple bond, followed by stereospecificalkoxycarbonylation, strictly resulting in E-stereochemistry. The structures of representativeoxazolines and bisoxazolines have been determined by X-ray diffraction analysis.
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