The Pictet-Spengler Reaction of Nb-Hydroxytryptamines and Cysteinals. II. Temperature Effects, Stereochemistry and Mechanism

Jinjun LIU; Masako NAKAGAWA; Koreharu OGATA; Tohru HINO

doi:10.1248/cpb.39.1672

The Pictet-Spengler Reaction of N_b-Hydroxytryptamines and Cysteinals. II. Temperature Effects, Stereochemistry and Mechanism

Jinjun LIU, Masako NAKAGAWA, Koreharu OGATA, Tohru HINO

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Keywords: Pictet-Spengler reaction, N_b-hydroxytryptamine, cysteinal, N_b-hydroxy-β-carboline, nitrone, spiroindolenine, mechanism, temperature effect

JOURNAL FREE ACCESS

1991 Volume 39 Issue 7 Pages 1672-1676

DOI https://doi.org/10.1248/cpb.39.1672

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Abstract

The effect of temperature on the Pictet-Spengler reaction of N_b-hydroxytryptamines (1) and cysteinals (2) has been examined. The optically active nitrones (3), obtained from 1 and 2, gave the corresponding N_b-hydroxy-β-carbolines (4α and 4β) exclusively at -78°C in the presence of an excess of trifluoroacetic acid. The mechanism is discussed in relation to the stereochemistry.

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