Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet–Spengler-Type Reactions

详细信息    查看全文

• 作者：Casper L. Hansen ; Ragnhild G. Ohm ; Lasse B. Olsen ; Erhad Ascic ; David Tanner ; Thomas E. Nielsen
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：December 2, 2016
• 年：2016
• 卷：18
• 期：23
• 页码：5990-5993
• 全文大小：318K
• ISSN：1523-7052

文摘

A synthetic strategy for the synthesis of chiral tetrahydrocarbazoles (THCAs) has been developed. The strategy relies on two types of 6-exo-trig cyclization of 3-substituted indole substrates. Enantioselective domino Friedel–Crafts-type reactions leading to THCAs can be catalyzed by chiral phosphoric acid derivatives (with up to >99% ee), and the first examples of exocyclic Pictet–Spengler reactions to form THCAs are reported.