Enantioselective BINOL-Phosphoric Acid Catalyzed Pictet−Spengler Reactions of N-Benzyltryptamine

详细信息    查看全文

• 作者：Nishant V. Sewgobind ; Martin J. Wanner ; Steen Ingemann ; René ; de Gelder ; Jan H. van Maarseveen ; Henk Hiemstra
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：August 15, 2008
• 年：2008
• 卷：73
• 期：16
• 页码：6405-6408
• 全文大小：190K
• 年卷期：v.73,no.16(August 15, 2008)
• ISSN：1520-6904

文摘

Optically active tetrahydro-β-carbolines were synthesized via an (R)-BINOL-phosphoric acid-catalyzed asymmetric Pictet−Spengler reaction of N-benzyltryptamine with a series of aromatic and aliphatic aldehydes. The tetrahydro-β-carbolines were obtained in yields ranging from 77% to 97% and with ee values up to 87%. The triphenylsilyl-substituted BINOL-phosphoric acid proved to be the catalyst of choice for the reaction with aromatic aldehydes. For the aliphatic aldehydes, 3,5-bistrifluoromethylphenyl-substituted BINOL-phosphoric acid was identified as the best catalyst.