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1978•Bulletin of the Chemical Society of JapanRequires access

Optical Activation of 2-Phenylpropionaldehyde via Some 2-Substituted Pyrrolidine Enamines

Hajime Matsushita, Yasuko Tsujino, Masao Noguchi, Masahiko Saburi, Sadao Yoshikawa

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Abstract

Abstract Optical activation of 2-phenylpropionaldehyde (PPA) via enamines using l-proline derivatives as amine components was studied. S(+)-PPA was obtained when R(−)-2-methylpyrrolidine and S(−)-2-ethoxycarbonylpyrrolidine were used, while R(−)-PPA was obtained when S(−)-prolinamide, N-(l-prolyl)pyrrolidine, N-(l-prolyl)piperidine, S(+)-2-(1-pyrrolidinylmethyl)pyrrolidine, and S(+)-2-(piperidinomethyl)pyrrolidine were used. This suggests that there are two mechanisms for optical activation.

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What this paper is about

Abstract Optical activation of 2-phenylpropionaldehyde (PPA) via enamines using l-proline derivatives as amine components was studied. S(+)-PPA was obtained when R(−)-2-methylpyrrolidine and S(−)-2-ethoxycarbonylpyrrolidine were used, while R(−)-PPA was obtained when S(−)-prolinamide, N-(l-prolyl)pyrrolidine, N-(l-prolyl)piperidine, S(+)-2-(1-pyrrolidinylmethyl)pyrrolidine, and S(+)-2-(piperidinomethyl)pyrrolidine were used. This suggests that there are two mechanisms for optical activation.

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Available abstract

Abstract Optical activation of 2-phenylpropionaldehyde (PPA) via enamines using l-proline derivatives as amine components was studied. S(+)-PPA was obtained when R(−)-2-methylpyrrolidine and S(−)-2-ethoxycarbonylpyrrolidine were used, while R(−)-PPA was obtained when S(−)-prolinamide, N-(l-prolyl)pyrrolidine, N-(l-prolyl)piperidine, S(+)-2-(1-pyrrolidinylmethyl)pyrrolidine, and S(+)-2-(piperidinomethyl)pyrrolidine were used. This suggests that there are two mechanisms for optical activation.

Key concepts: Pyrrolidine, Chemistry, Piperidine, Amine gas treating, Proline, Stereochemistry, Enamine, Medicinal chemistry

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