An Exploration of the Metal Oxide-assisted Decomposition and Rearrangement of N-Acyl-1,3-oxazolidin-2-ones Leading to 2-Aryl-2-oxazolines [1]

Author:

Deshpande Ankur A.1,Gossagea Robert A.2,Jackson Sarah M.1,Quail J. Wilson3,Sadowy Amber L.1,Yadav Paras N.1

Affiliation:

1. Department of Chemistry, Acadia University, Wolfville NS B4P 2R6, Canada

2. Department of Chemistry & Biology, Ryerson University, 350 Victoria Street, Toronto ON M5K 2B3, Canada

3. Department of Chemistry, University of Saskatchewan, Saskatoon SK S7N 5C9, Canada

Abstract

An exploration into the utility of the thermally-induced (metal oxide-mediated) CO2 extrusion and subsequent rearrangement of N-acyl-1,3-oxazolidin-2-ones to form 2-aryl(alkyl)-2-oxazolines is described. The reaction is found to give moderate yields of the corresponding 2-oxazolines. Attempts to employ the above methodology to give enantiopure (R)- or (S)-2,5-diphenyl-2-oxazoline (the latter form being the natural product Oxytriphine) from enantiopure (and crystallographically characterised) (S)-N-benzoyl-5-phenyl-2-oxazolidinone led to the isolation of an essentially racemic product. These protocols are compared to other common methods used to form the oxazoline ring system and are placed into context with previous investigations of such ring forming reactions.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

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