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Synthesis of highly substituted γ-butyrolactones by a gold-catalyzed cascade reaction of benzyl esters

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Abstract Easily accessible benzylic esters of 3-butynoic acids in a gold-catalyzed cyclization/rearrangement cascade reaction provided 3-propargyl ?-butyrolactones with the alkene and the carbonyl group not being conjugated. Crossover experiments showed that the formation of the new C?C bond is an i...

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Bibliographic Details
Main Authors: Blanco Jaimes, Maria Camila (Author) , Ahrens, Alexander (Author) , Pflästerer, Daniel (Author) , Rudolph, Matthias (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 2015
In: Chemistry - a European journal
Year: 2014, Volume: 21, Issue: 1, Pages: 427-433
ISSN:1521-3765
DOI:10.1002/chem.201402524
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201402524
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201402524
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Author Notes:Maria Camila Blanco Jaimes, Alexander Ahrens, Daniel Pflästerer, Matthias Rudolph, and A. Stephen K. Hashmi
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Summary:Abstract Easily accessible benzylic esters of 3-butynoic acids in a gold-catalyzed cyclization/rearrangement cascade reaction provided 3-propargyl ?-butyrolactones with the alkene and the carbonyl group not being conjugated. Crossover experiments showed that the formation of the new C?C bond is an intermolecular process. Initially propargylic?benzylic esters were used, but alkyl-substituted benzylic esters worked equally well. In the case of the propargylic?benzylic products, a simple treatment of the products with aluminum oxide initiated a twofold tautomerization to the allenyl-substituted ?-butyrolactones with conjugation of the carbonyl group, the olefin, and the allene. The synthetic sequence can be conducted stepwise or as a one-pot cascade reaction with similar yields. Even in the presence of the gold catalyst the new allene remains intact.
Item Description:First published: 28 October 2014
Im Titel wird gamma als griechischer Buchstabe dargestellt
Gesehen am 23.06.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201402524

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