Stereocontrol in the synthesis of cyclic amino acids: a new ligand for directed hydrogenation through hydrogen bonding

Organic & Biomolecular Chemistry
Vasudeva Rao GandiRoderick W Bates

Abstract

A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.

References

May 10, 1967·Journal of the American Chemical Society·B J MagerleinF Kagan
Apr 30, 1993·Journal of Medicinal Chemistry·J ZemlickaJ P Ballesta
Jul 17, 2001·Bioorganic & Medicinal Chemistry Letters·J Cossy, D Belotti
Mar 29, 2003·The Journal of Organic Chemistry·Luigi AurelioMarianne M Sleebs
May 10, 2003·The Journal of Organic Chemistry·Juan R Del Valle, Murray Goodman
Jan 18, 2007·Journal of the American Chemical Society·Jason C RechJonathan A Ellman
Sep 7, 2007·The Journal of Organic Chemistry·Carlos AlegretAntoni Riera
Nov 13, 2007·Angewandte Chemie·Tomás Smejkal, Bernhard Breit
Jun 19, 2012·Journal of the American Chemical Society·Philipp C RoosenMilton R Smith
Mar 23, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Fushi ZhangPi-Tai Chou
Sep 6, 2014·Organic Letters·Heather J JohnstonAlison N Hulme
Jan 31, 2015·Journal of Natural Products·Francisco Javier Ortíz-LópezFernando Reyes
Nov 1, 2017·Journal of the American Chemical Society·Kazimer L SkubiTehshik P Yoon

❮ Previous
Next ❯

Methods Mentioned

BETA
X-Ray
ion exchange chromatography

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.

Related Papers

Journal of Pharmaceutical Sciences
M FREIFELDER, G R STONE
The Journal of Organic Chemistry
Q XuY Souma
Journal of the Chemical Society. Perkin Transactions 1
G B HowarthJ K Jones
© 2022 Meta ULC. All rights reserved