Effect of pH on the regioselectivity of Pictet-Spengler reactions of 3-hydroxyphenethylamines with formaldehyde and acetaldehyde

HA Bates, K Bagheri, PM Vertino

Index: Bates, Hans A.; Bagheri, Kourosh; Vertino, Paula M. Journal of Organic Chemistry, 1986 , vol. 51, # 15 p. 3061 - 3063

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Citation Number: 27

Abstract

The Pictet-Spengler condensation of 3-alkoxyphenethylamines or 3- hydroxyphenethylamines 1 with aldehydes is widely utilized in the synthesis of tetrahydroisoquinolines' and also serves as the biosynthetic route to these alkaloids. 2 Cyclization has generally been reported to proceed para to the activating 3-alkoxy or 3- hydroxy group, thereby generating 6-alkoxy-or 6-hydroxytetrahydroisoquinolines (ie 2 or 4 ...