%0 Journal Article %A Blank, Nancy %A Opatz, Till %D 2011 %T Enantioselective Synthesis of Tetrahydroprotoberberines and Bisbenzylisoquinoline Alkaloids from a Deprotonated α-Aminonitrile %U https://acs.figshare.com/articles/journal_contribution/Enantioselective_Synthesis_of_Tetrahydroprotoberberines_and_Bisbenzylisoquinoline_Alkaloids_from_a_Deprotonated_Aminonitrile/2576011 %R 10.1021/jo201871c.s001 %2 https://acs.figshare.com/ndownloader/files/4219516 %K nonracemic precursors %K AminonitrileUnder %K deprotonated %K armepavine %K alkaloids %K Tetrahydroprotoberberine %K Bisbenzylisoquinoline Alkaloids %K dimethoxy %K laudanidine %K tetrahydroprotoberberine %K tetrahydropseudoepiberberine %K material %K laudanosine %K Noyori %K dihydroisoquinoline %K Ullmann diaryl ether syntheses %K Deprotonated %K dimeric %K preparation %K transfer hydrogenation %K tetramethylmagnolamine %K alkylation %K Enantioselective Synthesis %K corytenchine %X Under controlled conditions, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile can be quantitatively deprotonated in the α-position. Its alkylation directly furnishes 3,4-dihydroisoquinolines which can serve as starting materials for the preparation of various alkaloids. Here, the preparation of the benzylisoquinolines (+)-laudanidine, (+)-armepavine, and (+)-laudanosine as well as the tetrahydroprotoberberines (−)-corytenchine and (−)-tetrahydropseudoepiberberine using Noyori’s asymmetric transfer hydrogenation are described. The dimeric alkaloids (+)-O-methylthalibrine and (+)-tetramethylmagnolamine were obtained from nonracemic precursors in Ullmann diaryl ether syntheses. %I ACS Publications