Journal
ORGANIC LETTERS
Volume 17, Issue 10, Pages 2334-2337Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00809
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Funding
- JSPS KAKENHI [22225004, 24350079, 26620143]
- GCOE Program
- Grants-in-Aid for Scientific Research [26620143] Funding Source: KAKEN
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Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.
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