Novel, Chiral, and Enantiopure C2-Symmetric Thioureas Promote Asymmetric Protio-Pictet-Spengler Reactions by Anion-Binding Catalysis

被引：8

作者：

Retini, Michele ^{[1
]}

Bartoccini, Francesca ^{[1
]}

Zappia, Giovanni ^{[1
]}

Piersanti, Giovanni ^{[1
]}

机构：

[1] Univ Urbino Carlo Bo, Dipartimento Sci Biomol, Pzza Rinascimento 6, I-61029 Urbino, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 05期

关键词：

Anion-binding; Organocatalysis; Ion-pairing; Pictet-Spengler reaction; Synthetic methods; C-H; NONCOVALENT INTERACTIONS; ORGANOCATALYSIS; DEAROMATIZATION; RECOGNITION; ACTIVATION;

D O I：

10.1002/ejoc.202001501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Although anion-binding processes are well-known for their crucial role in molecular recognition, they have only recently been utilized for catalysis. Herein, a new class of chiral, enantiopure C-2-symmetrical thioureas that, in combination with 4-methoxybenzoic acid, promotes the enantioselective protio-Pictet-Spengler reaction to provide unprotected tetrahydro-beta-carbolines in good yields (40-93 %) and moderate-to-high enantioselectivities (34-95 % ee) in one step from tryptamine and aldehyde derivatives is described. The formation of a chiral catalyst-anion complex was explored by H-1 NMR.

引用

页码：825 / 829

页数：5

共 60 条

[1] Influence of the Substitution and Conformation of C-H-Bond-Based Bis-Triazole Acceptors in Anion-Binding Catalysis [J].