Abstract
Highly Z-selective syntheses of oxazolidin-2-ones from propargylic alcohols containing internal alkynes and phenyl isocyanate were achieved by using a combination of silver acetate and N,N-dimethylaminopyridine. The catalytic system was applied to propargylic alcohols containing alkyl-substituted alkyne groups. By considering the results in the presence and absence of an electron-withdrawing group on the aromatics, it was shown that the silver catalyst effectively activates the C≡C triple bond by acting as a π-Lewis acid to produce the corresponding oxazolidinones with high Z-selectivities.
Original language | English |
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Article number | st-2015-u0506-l |
Pages (from-to) | 2447-2450 |
Number of pages | 4 |
Journal | Synlett |
Volume | 26 |
Issue number | 17 |
DOIs | |
Publication status | Published - Oct 22 2015 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Organic Chemistry