Recent Developments in Transition-Metal-Catalyzed Asymmetric Hydrogenation of Enamides,Synthesis

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Recent Developments in Transition-Metal-Catalyzed Asymmetric Hydrogenation of Enamides
Synthesis ( IF 2.2 ) Pub Date : 2020-10-20 , DOI: 10.1055/s-0040-1705939
Phannarath Phansavath ₁ , Virginie Ratovelomanana-Vidal ₁ , Sudipta Ponra ₁ , Bernard Boudet ₂

Affiliation

Dedicated to Professor H. B. Kagan on the occasion of his birthday for his outstanding contribution to asymmetric catalysis and organometallic chemistry

Abstract

The catalytic asymmetric hydrogenation of prochiral olefins is one of the most widely studied and utilized transformations in asymmetric synthesis. This straightforward, atom economical, inherently direct and sustainable strategy induces chirality in a broad range of substrates and is widely relevant for both industrial applications and academic research. In addition, the asymmetric hydrogenation of enamides has been widely used for the synthesis of chiral amines and their derivatives. In this review, we summarize the recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of enamides.

1 Introduction

2 Asymmetric Hydrogenation of Trisubstituted Enamides

2.1 Ruthenium Catalysts

2.2 Rhodium Catalysts

2.3 Iridium Catalysts

2.4 Nickel Catalysts

2.5 Cobalt Catalysts

3 Asymmetric Hydrogenation of Tetrasubstituted Enamides

3.1 Ruthenium Catalysts

3.2 Rhodium Catalysts

3.3 Nickel Catalysts

4 Asymmetric Hydrogenation of Terminal Enamides

4.1 Rhodium Catalysts

4.2 Cobalt Catalysts

5 Rhodium-Catalyzed Asymmetric Hydrogenation of Miscellaneous Enamides

6 Conclusions

Publication History

Received: 08 July 2020

Accepted after revision: 26 August 2020

Publication Date:
20 October 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

过渡金属催化酰胺的不对称氢化的最新进展

致敬HB Kagan教授诞辰之际，他对不对称催化和有机金属化学的杰出贡献

抽象

前手性烯烃的催化不对称氢化是不对称合成中研究最广泛和应用最广泛的转化之一。这种简单，原子经济，内在直接和可持续的策略可在多种基质中引发手性，并且与工业应用和学术研究都息息相关。另外，烯酰胺的不对称氢化已广泛用于手性胺及其衍生物的合成。在这篇综述中，我们总结了该领域的最新工作，重点是开发新的催化系统，以及将这些不对称还原反应扩展到新型酰胺类。

1引言

2三取代酰胺的不对称氢化

2.1钌催化剂

2.2铑催化剂

2.3铱催化剂

2.4镍催化剂

2.5钴催化剂

3四取代酰胺的不对称氢化

3.1钌催化剂

3.2铑催化剂

3.3镍催化剂

4末端酰胺的不对称氢化