Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 2, Pages 920-927Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502404y
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Funding
- European Social Fund within the project Support for the implementation of doctoral studies at Riga Technical University
- European Regional Development Fund [ERAF 2010/2DP/2.1.1.1.0./10/APIA/VIAA/074]
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Disubstituted allylic bis-imidates undergo Lewis acid catalyzed or spontaneous cyclization to oxazolines, which are precursors of unsaturated amino alcohols. Stereoselectivity of the cyclization is mainly determined by the substrate configuration. Highly selective cis-oxazoline formation is achieved starting from anti-E-bis-imidates while trans-oxazoline predominantly forms from anti-Z-bis-imidates. On the basis of DFT calculations, the stereoselectivity trends can be explained by the formation of the energetically most stable carbenium ion conformation, followed by the cyclization via most favorable bond rotations.
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