Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes
Allyl 3,3-dimethylcyclopropenylcarbinyl ethers or sulfonamides undergo gold-catalyzed cycloisomerization leading to 5-isopropylidene-3-oxa- and 3-azabicyclo[4.1.0]heptanes in excellent yields and with high diastereoselectivities. These reactions constitute the first examples of intramolecular cyclop...
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| Veröffentlicht in: | Organic letters 2010-09, Vol.12 (18), p.4144-4147 |
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| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | Allyl 3,3-dimethylcyclopropenylcarbinyl ethers or sulfonamides undergo gold-catalyzed cycloisomerization leading to 5-isopropylidene-3-oxa- and 3-azabicyclo[4.1.0]heptanes in excellent yields and with high diastereoselectivities. These reactions constitute the first examples of intramolecular cyclopropanation of an alkene by a gold carbene generated by electrophilic ring opening of a cyclopropene in the presence of gold(I) chloride. |
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| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/ol101741f |