Escaping from Flatland: Stereoconvergent Synthesis of Three-Dimensional Scaffolds via Ruthenium(II)-Catalyzed Noyori-Ikariya Transfer Hydrogenation

被引：59

作者：

Cotman, Andrej Emanuel ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Pharm, Askerceva 7, Ljubljana 1000, Slovenia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 01期

关键词：

asymmetric catalysis; chirality; drug design; hydrogenation; ruthenium; ASYMMETRIC TRANSFER HYDROGENATION; DYNAMIC KINETIC RESOLUTION; ENANTIOSELECTIVE SYNTHESIS; SELECTIVE INHIBITOR; KETONES; ACCESS; DERIVATIVES; CATALYST; DESIGN; DESYMMETRIZATION;

D O I：

10.1002/chem.202002779

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Noyori-Ikariya-type ruthenium(II)-catalysts for asymmetric transfer hydrogenation (ATH) have been known for 25 years and have proved as a well-behaved and user-friendly platform for the synthesis of chiral secondary alcohols. A progress has been made in the past five years in understanding the asymmetric reduction of complex ketones, where up to four stereocenters can be controlled in a single chemical transformation. Intriguing multi-chiral molecular architectures are therefore available in few well understood and robust synthetic steps from commercially available building blocks and possess handles for additional functionalization. The aim of this Review is to showcase the availability of three-dimensional scaffolds and homochiral lead-like compounds via ATH and inspire their direct use in drug discovery endeavors. Basic mechanistic insights are provided to demystify the stereo-chemical outcomes, as well as examples of diastereoselective transformations of enantiopure alcohols to give a feeling of how these rigid non-planar molecules can be further elaborated.

引用

页码：39 / 53

页数：15

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