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ChemInform Abstract: OPTICAL ACTIVATION OF 2‐PHENYLPROPIONALDEHYDE VIA SOME 2‐SUBSTITUTED PYRROLIDINE ENAMINES

H. MATSUSHITA, Yasuko Tsujino, Masao Noguchi, Masahiko Saburi, Sadao Yoshikawa

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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

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

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, Piperidine, Chemistry, Amine gas treating, Proline, Stereochemistry, Organic chemistry, Biochemistry

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ChemInform Abstract: OPTICAL ACTIVATION OF 2‐PHENYLPROPIONALDEHYDE VIA SOME 2‐SUBSTITUTED PYRROLIDINE ENAMINES — Research Paper | ScholarLens