Abstract
ALL previous attempts to synthesise an optically active carbon compound have been based on one principle they have involved the combination of an inactive compound, containing an ethylene linkage or a carbonyl group, with an optically active substance to form an ester or glucoside, and the subsequent treatment of this product in such a way as to attach two different groups to a previously ethenoid carbon atom so as to render it asymmetrical. As Prof. Japp and others have pointed out, the two possible isomerides should not necessarily be formed in equal quantities, so that on hydrolysing the new ester or glucoside one of the isomerides would preponderate, and therefore an optically active product should be obtained. Prof. Kipping reduced the bornyl ester of benzoyl formic acid to the bornyl ester of mandelic acid, hoping to obtain an optically active mandelic acid. Prof. Fischer and M. D. Slimmer added hydrogen cyanide to helicin; they then hydrolysed the nitrile and subsequently the glucoside, with the object of preparing active oxymandelic acid.
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A Directed Synthesis of an Asymmetric Compound . Nature 69, 401 (1904). https://doi.org/10.1038/069401a0
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DOI: https://doi.org/10.1038/069401a0