The Pictet-Spengler reaction of N(b)-hydroxytryptamines and cysteinals. II. Temperature effects, stereochemistry and mechanism

DOI: 10.1248/cpb.39.1672

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1672 - 1676 (1991)

Update date:2022-08-03

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Authors:

Liu Liu

Nakagawa

Ogata Ogata

Hino Hino

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Article abstract of DOI:10.1248/cpb.39.1672

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.

Full text of DOI:10.1248/cpb.39.1672

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