Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

Aaron E. May; Patrick H. Willoughby; Thomas R. Hoye

doi:10.1021/jo800076f

Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

Aaron E. May, Patrick H. Willoughby, Thomas R. Hoye

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

15 Scopus citations

Abstract

(Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

Original language	English (US)
Pages (from-to)	3292-3294
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	73
Issue number	8
DOIs	https://doi.org/10.1021/jo800076f
State	Published - Apr 18 2008

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title = "Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines",

abstract = "(Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.",

author = "May, \{Aaron E.\} and Willoughby, \{Patrick H.\} and Hoye, \{Thomas R.\}",

year = "2008",

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doi = "10.1021/jo800076f",

language = "English (US)",

volume = "73",

pages = "3292--3294",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

AU - May, Aaron E.

AU - Willoughby, Patrick H.

AU - Hoye, Thomas R.

PY - 2008/4/18

Y1 - 2008/4/18

N2 - (Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

AB - (Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

UR - https://www.scopus.com/pages/publications/42149113561

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U2 - 10.1021/jo800076f

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M3 - Article

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SN - 0022-3263

VL - 73

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EP - 3294

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

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