Synthesis 2021; 53(21): 3951-3962
DOI: 10.1055/s-0040-1719822
short review

Catalytic, Enantioselective Diamination of Alkenes

Zhong-Lin Tao
a   College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, P. R. of China
,
b   Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA
› Author Affiliations
Z.L.T. thanks the Fundamental Research Funds for the Central Universities. S.E.D. acknowledges the National Science Foundation (NSF CHE 1664376 and CHE 2102232) for generous financial support.


Dedicated to the memory of Prof. Kilian Muñiz, a pioneer in alkene functionalization chemistry.

Abstract

Enantioselective diamination of alkenes represents one of the most straightforward methods to access enantioenriched, vicinal diamines, which are not only frequently encountered in biologically active compounds, but also have broad applications in asymmetric synthesis. Although the analogous dihydroxylation of olefins is well-established, the development of enantioselective olefin diamination lags far behind. Nevertheless, several successful methods have been developed that operate by different reaction mechanisms, including a cycloaddition pathway, a two-electron redox pathway, and a radical pathway. This short review summarizes recent advances and identifies limitations, with the aim of inspiring further developments in this area.

1 Introduction

2 Cycloaddition Pathway

3 Two-Electron Redox Pathway

3.1 Pd(0)/Pd(II) Diamination

3.2 Pd(II)/Pd(IV) Diamination

3.3 I(I)/I(III) Diamination

3.4 Se(II)/Se(IV) Diamination

4 One-Electron Radical Pathway

4.1 Cu-Catalyzed Diamination

4.2 Fe-Catalyzed Diamination

5 Summary and Outlook



Publication History

Received: 31 May 2021

Accepted after revision: 01 July 2021

Article published online:
27 July 2021

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