<> "The repository administrator has not yet configured an RDF license."^^ . <> . . "The Application of the Titanium-Catalyzed Hydroamination of Alkynes toward the Synthesis of Benzylisoquinoline Derivatives"^^ . "The enantioselective synthesis of (+)-(S)-laudanosine (101) and (–)-(S)-xylopinine (102) were achieved successfully in 7 steps from commercially available homoveratylamine (86) in 62% and 51% yield, respectively. The key intermediate aminoalkyne 123 was accessed easily by coupling aryl iodide 115 and alkyne 121 using a Sonogashira reaction. Dihydroisoquinoline 124 was obtained by intramolecular hydroamination of the aminoalkyne 123. Employing Noyori´s reduction protocol, the absolute configuration at C-1 of the benzylisoquinoline was introduced with 93% ee. Finally, methylation of norlaudanosine (146) by a reductive amination protocol afforded (+)-(S)-laudanosine (101). Alternatively, formation of the berberin-bridge using a Pictet-Spengler reaction afforded (–)-(S)-xylopinine (102). The strategy was also applied to synthesize benzylisoquinolines with electron-deficient A-rings. 5-Trifluoromethyl-benzylisoquinoline (174) was successfully synthesized in 8 steps from commercially available 4-bromo-trifluorotoluene (162) in 20% yield. Both Sonogashira reaction and hydroamination gave the desired products in excellent yields. Moreover, 6,7-difluoro-benzylisoquinoline (182), was synthesized following a similar route from commercially available o-bromo-benzoic acid (175) in 19% yield for the seven steps. "^^ . "2006" . . . . . . . . "Didin"^^ . "Mujahidin"^^ . "Didin Mujahidin"^^ . . . . . . "The Application of the Titanium-Catalyzed Hydroamination of Alkynes toward the Synthesis of Benzylisoquinoline Derivatives (PDF)"^^ . . . "Dissertation_D_Mujahidin_complete.pdf"^^ . . . "The Application of the Titanium-Catalyzed Hydroamination of Alkynes toward the Synthesis of Benzylisoquinoline Derivatives (Other)"^^ . . . . . . "indexcodes.txt"^^ . . . "The Application of the Titanium-Catalyzed Hydroamination of Alkynes toward the Synthesis of Benzylisoquinoline Derivatives (Other)"^^ . . . . . . "lightbox.jpg"^^ . . . "The Application of the Titanium-Catalyzed Hydroamination of Alkynes toward the Synthesis of Benzylisoquinoline Derivatives (Other)"^^ . . . . . . "preview.jpg"^^ . . . "The Application of the Titanium-Catalyzed Hydroamination of Alkynes toward the Synthesis of Benzylisoquinoline Derivatives (Other)"^^ . . . . . . "medium.jpg"^^ . . . "The Application of the Titanium-Catalyzed Hydroamination of Alkynes toward the Synthesis of Benzylisoquinoline Derivatives (Other)"^^ . . . . . . "small.jpg"^^ . . "HTML Summary of #6562 \n\nThe Application of the Titanium-Catalyzed Hydroamination of Alkynes toward the Synthesis of Benzylisoquinoline Derivatives\n\n" . "text/html" . . . "540 Chemie"@de . "540 Chemistry and allied sciences"@en . .