Rhodium-Azavinylcarbene: A Versatile Synthon-Enabling Divergent Synthesis of Nitrogen Heterocycles

Yuanhao Wang; Xiaoqiang Lei; Yefeng Tang

doi:10.1055/s-0034-1380444

Synlett, Table of Contents

Synlett 2015; 26(15): 2051-2059
DOI: 10.1055/s-0034-1380444

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Rhodium-Azavinylcarbene: A Versatile Synthon-Enabling Divergent Synthesis of Nitrogen Heterocycles

Yuanhao Wang

^aThe Comprehensive AIDS Research Center and Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 P. R. of China Email: yefengtang@tsinghua.edu.cn

,

Xiaoqiang Lei

^aThe Comprehensive AIDS Research Center and Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 P. R. of China Email: yefengtang@tsinghua.edu.cn

,

Yefeng Tang*

^aThe Comprehensive AIDS Research Center and Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 P. R. of China Email: yefengtang@tsinghua.edu.cn

^bCollaborative Innovation Center for Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China

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Abstract

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Abstract

Over the past several years, rhodium-azavinylcarbene (Rh-AVC) has grown into an enabling synthon for the synthesis of diverse nitrogen heterocycles. Herein we present an overview of our recent achievements in this field, including the Rh-AVC-promoted formal [4+3], [3+3], and [3+2] cycloadditions. These reactions allow for the efficient synthesis of several classes of important nitrogen heterocycles, such as azepines, pyrroles, and pyrazines. Some relevant works from other groups are also briefly discussed.

1 Introduction

2 Formal [4+3] and [3+2] Cycloadditions of 1,2,3-Triazoles with 1,3-Dienes

3 Formal [3+2] Cycloadditions of 1,2,3-Triazoles with Silyl or Alkyl Enol Ethers

4 Formal [3+3] and [3+2] Cycloadditions of 1,2,3-Triazoles with 2H-Azirines

5 Conclusion and Perspective

Key words

heterocycle - cycloaddition - 1,2,3-triazole - carbene - pyrrole

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