Iridium-Catalyzed Asymmetric Umpolung Allylation of N-Fluor­enyl Imines to Prepare 1,4-Disubstituted Homoallylic Amines

Liqiang Wan; Lan Tian; Jie Liu; Dawen Niu

doi:10.1055/s-0036-1588514

Synlett, Table of Contents

Synlett 2017; 28(16): 2051-2056
DOI: 10.1055/s-0036-1588514

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Iridium-Catalyzed Asymmetric Umpolung Allylation of N-Fluorenyl Imines to Prepare 1,4-Disubstituted Homoallylic Amines

Authors

Liqiang Wan

Department of Emergency, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China Email: niudawen@scu.edu.cn
Lan Tian

Department of Emergency, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China Email: niudawen@scu.edu.cn
Jie Liu

Department of Emergency, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China Email: niudawen@scu.edu.cn
Dawen Niu*

Department of Emergency, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China Email: niudawen@scu.edu.cn

Abstract

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Abstract

The discovery and development of an Ir-catalyzed asymmetric umpolung allylation of imines is discussed here. This method produces 1,4-disubstituted homoallylic amines, a class of compounds that are difficult to access by conventional methods. This reaction proceeds through a sequence involving an allylation and a 2-aza-Cope rearrangement event. The unique mechanistic feature of this reaction could be the reason for its broad substrate scope. The products of this reaction are useful intermediates for various bioactive and natural products. Besides its immediate synthetic utility, we expect this transformation to inspire the development of other umpolung functionalizations of imines and Ir-catalyzed asymmetric allylic substitution (AAS) reactions.

1 Introduction

2 Reaction Discovery

3 Substrate Scope

4 Conclusion

Key words

iridium - allylation - umpolung - imine - enantioselectivity

Full Text

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Iridium-Catalyzed Asymmetric Umpolung Allylation of N-Fluor­enyl Imines to Prepare 1,4-Disubstituted Homoallylic Amines

Authors

Iridium-Catalyzed Asymmetric Umpolung Allylation of N-Fluorenyl Imines to Prepare 1,4-Disubstituted Homoallylic Amines