Application of an intramolecular Stetter reaction to access trans,syn,trans-fused pyrans

Christopher S.P. McErlean; Anthony C. Willis

doi:10.1055/s-0028-1087519

Application of an intramolecular Stetter reaction to access trans,syn,trans-fused pyrans

Christopher S.P. McErlean, Anthony C. Willis

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

The use of a commercially available thiazolium salt facilitated an intramolecular Stetter reaction between an aliphatic aldehyde and an acrylate unit, which delivered a trans,syn-fused bicyclic pyranone in high yield as a single diastereomer. The pyranone was used to synthesize a trans,syn,trans-fused polycyclic ether array and was ring expanded to give the corresponding oxepanone.

Original language	English
Pages (from-to)	233-236
Number of pages	4
Journal	Synlett
Issue number	2
DOIs	https://doi.org/10.1055/s-0028-1087519
Publication status	Published - Jan 2009

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abstract = "The use of a commercially available thiazolium salt facilitated an intramolecular Stetter reaction between an aliphatic aldehyde and an acrylate unit, which delivered a trans,syn-fused bicyclic pyranone in high yield as a single diastereomer. The pyranone was used to synthesize a trans,syn,trans-fused polycyclic ether array and was ring expanded to give the corresponding oxepanone.",

keywords = "Carbenes, Diastereoselectivity, Fused-ring systems, Ring closure, Umpolung",

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N2 - The use of a commercially available thiazolium salt facilitated an intramolecular Stetter reaction between an aliphatic aldehyde and an acrylate unit, which delivered a trans,syn-fused bicyclic pyranone in high yield as a single diastereomer. The pyranone was used to synthesize a trans,syn,trans-fused polycyclic ether array and was ring expanded to give the corresponding oxepanone.

AB - The use of a commercially available thiazolium salt facilitated an intramolecular Stetter reaction between an aliphatic aldehyde and an acrylate unit, which delivered a trans,syn-fused bicyclic pyranone in high yield as a single diastereomer. The pyranone was used to synthesize a trans,syn,trans-fused polycyclic ether array and was ring expanded to give the corresponding oxepanone.

KW - Carbenes

KW - Diastereoselectivity

KW - Fused-ring systems

KW - Ring closure

KW - Umpolung

UR - https://www.scopus.com/pages/publications/62349083420

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DO - 10.1055/s-0028-1087519

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JO - Synlett

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ER -

Application of an intramolecular Stetter reaction to access trans,syn,trans-fused pyrans

Abstract

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