Stereoselective Synthesis of Baylis−Hillman-Type Adducts via Allenolates Generated by Acyl Migration
The rearrangement of the carbamoyl group in allenyl carbamate 1 in the presence of n-BuLi in situ generates the allenolate 3, which is subsequently intercepted with aromatic aldehydes furnishing (Z)- or (E)-configured Baylis−Hillman-type adducts 4 or 5. The double bond isomers can be interconverted...
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| Veröffentlicht in: | Organic letters 2004-10, Vol.6 (22), p.4005-4008 |
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| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | The rearrangement of the carbamoyl group in allenyl carbamate 1 in the presence of n-BuLi in situ generates the allenolate 3, which is subsequently intercepted with aromatic aldehydes furnishing (Z)- or (E)-configured Baylis−Hillman-type adducts 4 or 5. The double bond isomers can be interconverted by a retro aldol-type reaction. |
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| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/ol0483908 |