Studies in Stereochemistry. XX. dl-Phenylserinols : A New Synthesis and its Stereochemical Findings. (7). An Isomerization of dlthreo-2-Phenyl-4-α-hydroxybenzyl-2-oxazoline to dl-threo-4-Hydroxymethyl-2,5-diphenyl-2-oxazoline in Basic Media : The Correcti
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概要
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In the preceding paper of this series, it was tentatively assumed, while leaving some doubt, that dl-threo-2-phenyl-4-α-hydroxybenzyl-2-oxazoline isomerized into dl-2-benzamido-3-phenyl-2-propen-1-ol or dl-2-benzimido-3-phenylpropanol in basic media. In this paper, the structure of the isomerization product was corrected to dl-threo-2,5-diphenyl-4-hydroxymethyl-2-oxazoline by reexamination of chemical properties and final synthesis. The analogous isomerization observed in the optically active p-nitro analogs is a further support for the correction and a possible mechanism of the isomerization without Walden inversion was proposed. dl-threo-2,5-Diphenyl-4-benzoyloxymethyl-2-oxazoline was found to add benzoyl chloride causing ring opening with Walden inversion to give dl-erythro-2-dibenzoylamino-3-chloro-3-phenylpropyl benzoate.
- 公益社団法人日本薬学会の論文
- 1958-12-15
著者
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友枝 宗光
Eisai Co., Ltd.
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友枝 宗光
Eisai Co. Ltd.
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友枝 宗光
Pharmaceutical Institute, Medical Faculty, University of Kyushu
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