6533b833fe1ef96bd129b657

RESEARCH PRODUCT

Synthesis of (–)-(S)-Norlaudanosine, (+)-(R)-O,O-Dimethylcoclaurine, and (+)-(R)-Salsolidine by Alkylation of an α-Aminonitrile

Nancy BlankTill OpatzFrank Werner

subject

DeprotonationSalsolidineStereochemistryChemistryOrganic ChemistryEnantioselective synthesisPhysical and Theoretical ChemistryAlkylationCarbanionUmpolung

description

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)

https://doi.org/10.1002/ejoc.200700261