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Synthesis of (–)‐( S )‐Norlaudanosine, (+)‐( R )‐ O , O ‐Dimethylcoclaurine, and (+)‐( R )‐Salsolidine by Alkylation of an α‐Aminonitrile
Author(s) -
Werner Frank,
Blank Nancy,
Opatz Till
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700261
Subject(s) - chemistry , alkylation , carbanion , deprotonation , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ion
Abstract A short asymmetric synthesis of 1‐substituted 1,2,3,4‐tetrahydroisoquinoline alkaloids by deprotonation of an unprotected α‐aminonitrile and alkylation of the resulting carbanion followed by spontaneous elimination of HCN and asymmetric reduction is described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)