The formation of threo-2-benzamido-1-phenylpropan-1-ol from attempted cyclisation of its erythro-isomer is explained. In place of the expected 3-methyl-1-phenylisoquinoline, cyclisation yields 4-methyl-2,5-diphenyl-Δ2-oxazoline. Attempted isolation of the product via hydrochloride salt formation results in ring opening and eventual formation of threo-2-benzamido-1-phenylpropan-1-ol via a three-stage process.
A. O. Fitton and J. R. Frost, J. Chem. Soc., Perkin Trans. 1, 1974, 1153 DOI: 10.1039/P19740001153
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