Gold(I)-catalyzed domino reaction of allyl 2-en-4-ynyl ethers to 1,3,6-trien-4-yl ketones
The gold(I)-catalyzed reaction of allyl 2-en-4-ynyl ethers provides stereoselectively (Z)-1,3,6-trienes with an acyl substitutent in the 4-position. The reaction proceeds through an oxygen transfer along the chain and a clean allylic inversion. This complements the preceding work by Gagosz, who obta...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
March 7, 2013
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| In: |
ChemCatChem
Year: 2013, Volume: 5, Issue: 5, Pages: 1200-1204 |
| ISSN: | 1867-3899 |
| DOI: | https://doi.org/10.1002/cctc.201200787 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/cctc.201200787 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cctc.201200787 
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| Author Notes: | A. Stephen K. Hashmi, Katharina Graf, Martin Ackermann, and Frank Rominger |
| Summary: | The gold(I)-catalyzed reaction of allyl 2-en-4-ynyl ethers provides stereoselectively (Z)-1,3,6-trienes with an acyl substitutent in the 4-position. The reaction proceeds through an oxygen transfer along the chain and a clean allylic inversion. This complements the preceding work by Gagosz, who obtained furan derivatives in his investigation of similar substrates with terminal alkynyl groups.10, 16 The only drawback of this mechanistically new pathway is the instability of the products under the reaction conditions, which sometimes prevents their isolation in high yields. |
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| Item Description: | Gesehen am 08.10.2021 |
| Physical Description: | Online Resource |
| ISSN: | 1867-3899 |
| DOI: | https://doi.org/10.1002/cctc.201200787 |