Enantioselective Bromolactonization of Trisubstituted Olefinic Acids Catalyzed by Chiral Pyridyl Phosphoramides

Chemistry : a European Journal
Yasuhiro NishikawaOsamu Hara

Abstract

Enantioselective bromolactonization of trisubstituted olefinic acids producing synthetically useful chiral lactones with two contiguous asymmetric centers has remained mainly unexplored except for the 6-exo cyclization mode. In this work, the 5-exo- and 6-endo modes of bromocyclization of trisubstituted olefinic acids were enabled for the first time using N-bromosuccinimide and a pyridyl phosphoramide catalyst. The utility of the resulting bromolactones was demonstrated by transformations harnessing reactive alkyl bromide moieties without losing stereochemical information. Optimization studies and control experiments revealed that the basicity of pyridine moieties and presence of N-H protons in the phosphoramide species strongly affected both the reactivity and enantioselectivity parameters.

References

Jul 1, 1980·Proceedings of the National Academy of Sciences of the United States of America·A W AlbertsJ Springer
Feb 23, 2010·Journal of the American Chemical Society·Daniel C WhiteheadBabak Borhan
Mar 3, 2010·Journal of the American Chemical Society·Wei ZhangWeiping Tang
Aug 14, 2010·Proceedings of the National Academy of Sciences of the United States of America·Scott E Denmark, Matthew T Burk
Aug 31, 2010·Angewandte Chemie·Gemma E Veitch, Eric N Jacobsen
Oct 16, 2010·Journal of the American Chemical Society·Ling ZhouYing-Yeung Yeung
Oct 26, 2010·Angewandte Chemie·Kenichi MuraiHiromichi Fujioka
Feb 10, 2011·Organic Letters·Ulrich HenneckeRoland Fröhlich
May 5, 2011·Journal of the American Chemical Society·Ling ZhouYing-Yeung Yeung
Mar 7, 2012·Angewandte Chemie·Michael T Bovino, Sherry R Chemler
Apr 3, 2012·Journal of the American Chemical Society·Mark C Dobish, Jeffrey N Johnston
May 25, 2012·Chemistry : a European Journal·Kenichi MuraiHiromichi Fujioka
Jun 26, 2012·Journal of the American Chemical Society·Daniel H PaullStephen F Martin
Jul 27, 2012·Journal of the American Chemical Society·Yi-Ming WangF Dean Toste
Sep 25, 2012·Journal of the American Chemical Society·Yi An ChengYing-Yeung Yeung
Sep 27, 2012·Angewandte Chemie·Scott E DenmarkMatthew T Burk
Nov 15, 2012·Organic Letters·Kazutada IkeuchiToshiyuki Kan
Jan 15, 2013·Journal of the American Chemical Society·Feng ChenYing-Yeung Yeung
May 11, 2013·Journal of the American Chemical Society·Deshun HuangYian Shi
May 15, 2013·Chemistry : a European Journal·Atefeh GarzanBabak Borhan
Mar 7, 2014·Organic & Biomolecular Chemistry·Yi An ChengYing-Yeung Yeung
Apr 5, 2014·Journal of the American Chemical Society·Zhihai KeYing-Yeung Yeung
Sep 10, 2014·Chemical Communications : Chem Comm·Kenichi MuraiHiromichi Fujioka
Aug 8, 2015·Journal of the American Chemical Society·Hiromichi EgamiYoshitaka Hamashima
Jan 9, 2016·Chemistry : a European Journal·Yuji KawatoYoshitaka Hamashima
May 21, 2016·Chemical Reviews·Indranirekha SaikiaProdeep Phukan
Jun 11, 2016·Journal of the American Chemical Society·Kumar Dilip AshtekarBabak Borhan
Aug 27, 2016·The Journal of Organic Chemistry·Marius AursnesTrond V Hansen
Oct 12, 2016·Chemistry : a European Journal·Michael WilkingUlrich Hennecke
Jan 7, 2017·Journal of the American Chemical Society·Ramesh C Samanta, Hisashi Yamamoto
Feb 6, 2018·Journal of the American Chemical Society·Matthew T KnoweJeffrey N Johnston
Feb 10, 2018·Journal of the American Chemical Society·Hiromichi EgamiYoshitaka Hamashima
May 1, 2018·Journal of the American Chemical Society·Yanhui LuKazuaki Ishihara
May 3, 2018·Chemical Science·Nastaran Salehi MarzijaraniBabak Borhan

❮ Previous
Next ❯

Citations

Oct 2, 2020·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Yasuhiro Nishikawa
Jun 3, 2021·Nature Communications·Dibyendu MondalJared C Lewis
Aug 6, 2021·Journal of the American Chemical Society·Yuk-Cheung ChanYing-Yeung Yeung

❮ 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.