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

Chemistry : a European Journal
Andrej Emanuel Cotman

Abstract

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.

References

May 19, 2005·Journal of the American Chemical Society·Aidan M HayesMartin Wills
Oct 27, 2007·Accounts of Chemical Research·Takao Ikariya, A John Blacker
Oct 16, 2009·Journal of Medicinal Chemistry·Frank LoveringChristine Humblet
Feb 5, 2011·Nature·Philip J HajdukDavid R Spring
Aug 30, 2011·Journal of the American Chemical Society·Taichiro TougeTakao Ikariya
Jan 25, 2012·Angewandte Chemie·Alan NadinIan Churcher
Sep 28, 2013·Organic Letters·Rina SoniMartin Wills
Jun 20, 2015·Angewandte Chemie·Alexander T MurrayDavid R Carbery
Aug 28, 2015·Chemistry : a European Journal·Liping KuangPauline Chiu
Dec 23, 2015·Organic & Biomolecular Chemistry·J C Morris, C S P McErlean
Jan 20, 2016·Organic & Biomolecular Chemistry·Slavko RastBarbara Mohar
Mar 22, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Pavel A Dub, John C Gordon
Aug 16, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Hans G NeddenMartin Wills
Feb 16, 2017·ACS Medicinal Chemistry Letters·Christopher W PlummerSteven L Colletti
Jul 24, 2018·ACS Medicinal Chemistry Letters·Zahid Q BondayRobert M Campbell
Aug 14, 2018·The Journal of Organic Chemistry·Neil A StrotmanJoerg Deerberg
Aug 25, 2018·Nature Reviews. Drug Discovery·Jonas BoströmGyörgy M Keserü
Feb 8, 2019·Nature·Jiankun LyuJohn J Irwin

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.