596804-07-8

Upstream product

• 404962-08-9 3-[1-(4-hydroxy-pentyl)-propa-1,2-dienyl]-4-phenyl-oxazolidin-2-one 
• 93929-67-0 tert-butyl[(1S)-4-iodo-1-methylbutoxy]dimethylsilane 
• 100289-43-8 4-(tert-butyl-dimethyl-silanyloxy)-pentanal 
• 104871-08-1 4-(tert-butyl-dimethyl-silanyloxy)-pentan-1-ol 
• 171011-70-4 (S)-4-(tert-butyl-dimethyl-silanyloxy)-pent-2-yn-1-ol 
• 606965-07-5 3-{1-[4-(tert-butyl-dimethyl-silanyloxy)-pentyl]-propa-1,2-dienyl}-4-phenyl-oxazolidin-2-one 
• 256382-50-0 (4R)-4-phenyl-3-(1,2-propadienyl)-2-oxazolidinone 

Relevant academic research and scientific papers

NMR studies on epoxidations of allenamides. Evidence for formation of nitrogen-substituted allene oxide and spiro-epoxide via trapping experiments

Two epoxidations of chiral allenamides are described here. While treatment with m-CPBA led to highly stereoselective formation of an α-keto aminal that can be useful synthetically, DMDO oxidation led to conclusive evidence for both nitrogen-substituted allene oxide (via mono-epoxidation) and spiro-epoxide (via bis-epoxidation) using intramolecular nucleophilic trapping experiments. NMR studies provide reliable evidence for a 3-oxetanone that can be derived from the spiro-epoxide and also suggest the presence of an allene oxide. Despite a facile second epoxidation as evidenced by the predominant formation of the 3-oxetanone, in the presence of furan, [4 + 3] cycloaddition of the nitrogen-substituted allene oxide or oxyallyl cation with furan occurs faster than the second epoxidation efficiently leading to cycloadducts. This rate difference plays an invaluable role for the success of a stereoselective sequential epoxidation-[4 + 3] cycloaddition reaction via DMDO epoxidations of chiral allenamides.