Stereochemical Studies. XVIII. Nitrous Acid Deaminations of threo- and erythro-Phenylserine and Their Methyl Esters in Acetic Acid

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概要

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• Nitrous acid deaminations of threo-(Ia) and erythro-phenylserine methyl ester (Ib) gave methyl benzoylacetate (II) and methyl phenylmalonaldehydate (IX) by hydrogen migration and phenyl migration, respectively. Further reaction of IX afforded methyl α-hydroximinophenylacetates (IIIa-b) and N-nitrosooxazolidines (VIa-g). Deaminations of threo-(XIIIa) and erythro-phenylserine (XIIIb) were, however, highly specific and gave the corresponding α-acetoxy acid as the sole product with retention of configuration. The reaction paths involved in this study were discussed.

• 公益社団法人日本薬学会の論文
• 1972-09-25

著者

• 古賀 憲司

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• Koga Kenjiro

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University

• 楊 正勝

  Faculty of Pharmaceutical Sciences, University of Tokyo

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