Helvetica chimica acta

Diasteroselektive Hydroxyalkylierungen in 1??Stellung von Tetrahydroisochinolinen und Synthese von Aporphin??, Protoberberin??und Phthalid??Alkaloider

D Seebach, MP Isabelle, AS Max

Index: Seebach,Dieter; Huber, Isabelle M. P.; Syfrig, Max A. Helvetica Chimica Acta, 1987 , vol. 70, p. 1357 - 1379

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Citation Number: 48

Abstract

Unsubstituted and 6, 7-dialkoxy-N-pivaloyl-tetrahydroisoqu~ nolines 1-3 are converted to l- bromomagnesium derivatives by sequential treatment with 1-BuLi (-75"/THF) and MgBrz. 0Et2. Addition of the metalated tetrahydroisoquinolines to aliphatic or aromatic aldehydes occurs with relative topicity ul (Scheme 2). The I-hydroxyalkylated 2-pivaloyl- tetrahydroisoquinolines a of u-configuration thus obtained (14 examples) can be ...