Synthesis of 3-oxa- and 3-azabicyclo[4.1.0]heptanes by gold-catalyzed cycloisomerization of cyclopropenes | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

2828757

Reference Type

Journal Article

Title

Synthesis of 3-oxa- and 3-azabicyclo[4.1.0]heptanes by gold-catalyzed cycloisomerization of cyclopropenes

Author(s)

Miege, F; Meyer, C; Cossy, J

Year

2010

Is Peer Reviewed?

Journal

Organic Letters
ISSN: 1523-7060
EISSN: 1523-7052

Volume

Issue

Page Numbers

4144-4147

Language

English

PMID

20726564

DOI

10.1021/ol101741f

Abstract

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.