Chemical and Pharmaceutical Bulletin p. 1672 - 1676 (1991)
Update date:2022-08-03
Topics:
Liu
Nakagawa
Ogata
Hino
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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