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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Bibliographic Details
Published in:Organic letters 2010-09, Vol.12 (18), p.4144-4147
Main Authors: Miege, Frédéric, Meyer, Christophe, Cossy, Janine
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101741f