Pd/C-Catalyzed Dehydrogenative [3+2] Cycloaddition for the Synthesis of Functionalized Tropanes

被引：8

作者：

Wang, Hai-Jun ^{[1
]}

Guo, Lei ^{[1
]}

Zhu, Cheng-Feng ^{[1
]}

Luo, Yun-Fei ^{[1
]}

Li, You-Gui ^{[1
]}

Wu, Xiang ^{[1
]}

机构：

[1] Hefei Univ Technol, Anhui Prov Key Lab Adv Catalyt Mat & React Engn, Sch Chem & Chem Engn, Hefei 230009, Anhui, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 39期

基金：

中国国家自然科学基金;

关键词：

Palladium; Dehydrogenative; 3+2] Cycloaddition; Tropanes; Asymmetric; AROMATIZATION REACTION CASCADE; FUSED BETA-CARBOLINES; AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITIONS; ONE-POT; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; TERTIARY-AMINES; ALDER REACTION; CONSTRUCTION;

D O I：

10.1002/ejoc.201801147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd/C-catalyzed cascade approach for the synthesis of attractive benzo-fused tropanes was developed. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from amines and 1,3-dipolar cycloaddition. It allows the generation of structurally complex benzo-fused tropanes in good yields with excellent diastereoselectivities under mild reaction conditions. Preliminary results of asymmetric version of the reaction reveal that the copper catalyst and chiral monophosphoramidite ligand can furnish optically active products with moderate ee.

引用

页码：5456 / 5459

页数：4

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