Gold-Catalyzed Rearrangement of Allylic Oxonium Ylides: Efficient Synthesis of Highly Functionalized Dihydrofuran-3-ones

“Diazo” not needed: The title reaction results in the rearrangement of oxonium ylides, which were prepared from readily available homopropargylic allylic ethers instead of diazo compounds, through two different mechanisms: a concerted 2,3‐sigmatropic rearrangement, or a stepwise 1,4‐allyl migration...

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Veröffentlicht in:	Angewandte Chemie International Edition 2013-04, Vol.52 (15), p.4198-4202
Hauptverfasser:	Fu, Junkai, Shang, Hai, Wang, Zhaofeng, Chang, Le, Shao, Wenbing, Yang, Zhen, Tang, Yefeng
Format:	Artikel
Sprache:	eng
Schlagworte:	Allyl Compounds - chemical synthesis Allyl Compounds - chemistry carbenoids Catalysis Claisen rearrangement Ethers Furans - chemical synthesis Furans - chemistry gold Migration Molecular Structure Organogold Compounds - chemistry oxonium ylide Oxygen - chemistry sigmatropic rearrangement Stereoisomerism Synthesis
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Beschreibung
Zusammenfassung:	“Diazo” not needed: The title reaction results in the rearrangement of oxonium ylides, which were prepared from readily available homopropargylic allylic ethers instead of diazo compounds, through two different mechanisms: a concerted 2,3‐sigmatropic rearrangement, or a stepwise 1,4‐allyl migration followed by a Claisen rearrangement (see scheme).
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201208305