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 |
|---|---|
| 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 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
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Synthesis of Oxazolidin-2-ones by Tandem Cyclization of Propargylic Alcohols and Phenyl Isocyanate Promoted by Silver Catalysts as π-Lewis Acids. / Sekine, Kohei; Mawatari, Takanori; Yamada, Tohru.
In: Synlett, Vol. 26, No. 17, st-2015-u0506-l, 22.10.2015, p. 2447-2450.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Synthesis of Oxazolidin-2-ones by Tandem Cyclization of Propargylic Alcohols and Phenyl Isocyanate Promoted by Silver Catalysts as π-Lewis Acids
AU - Sekine, Kohei
AU - Mawatari, Takanori
AU - Yamada, Tohru
PY - 2015/10/22
Y1 - 2015/10/22
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84943555137&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84943555137&partnerID=8YFLogxK
U2 - 10.1055/s-0035-1560263
DO - 10.1055/s-0035-1560263
M3 - Article
AN - SCOPUS:84943555137
VL - 26
SP - 2447
EP - 2450
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 17
M1 - st-2015-u0506-l
ER -