Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination

ACS Catalysis
Zainab M KhoderSherry R Chemler

Abstract

A convenient copper-catalyzed intramolecular/intermolecular alkene diamination reaction to synthesize 3-aminomethyl-functionalized isoxazolidines under mild reaction conditions and with generally high levels of diastereoselectivity was achieved. This reaction demonstrates that previously underutilized unsaturated carbamates are good [Cu]-catalyzed diamination substrates. Sulfonamides, anilines, benzamide, morpholine, and piperidine can serve as the external amine source. This relatively broad amine range is attributed to the mild reaction conditions. Reduction of the N-O bond could also be achieved, revealing the corresponding 3,4-diamino-1-alcohols efficiently.

References

Nov 22, 2002·Organic Letters·Roderick W Bates, Kanicha Sa-Ei
Mar 14, 2003·Organic Letters·Fuk Yee Kwong, Stephen L Buchwald
Oct 9, 2007·Journal of the American Chemical Society·Wei Zeng, Sherry R Chemler
Dec 4, 2008·Journal of the American Chemical Society·Peter H FullerSherry R Chemler
Feb 26, 2009·The Journal of Organic Chemistry·Georgia S LemenJohn P Wolfe
Jul 31, 2010·Angewandte Chemie·Fatima C SequeiraSherry R Chemler
Aug 14, 2010·Organic Letters·Roderick W Bates, Yongna Lu
Jul 7, 2011·Journal of the American Chemical Society·Youssef HarrakAmadeu Llebaria
Aug 10, 2011·The Journal of Organic Chemistry·Katsuhiko MoriyamaHideo Togo
Sep 29, 2011·Angewandte Chemie·Caren RöbenKilian Muñiz
Aug 9, 2012·The Journal of Organic Chemistry·Shuklendu D KaryakarteSherry R Chemler
Aug 14, 2012·Tetrahedron·Sam de JongDuncan J Wardrop
Dec 19, 2012·The Journal of Organic Chemistry·Monissa C PaderesSherry R Chemler
Jan 29, 2013·The Journal of Organic Chemistry·Boris EgartConstantin Czekelius
Feb 27, 2013·The Journal of Organic Chemistry·Kilian Muñiz, Claudio Martínez
Mar 19, 2013·European Journal of Medicinal Chemistry·Jabeena KhazirH M Sampath Kumar
Jun 6, 2013·Journal of the American Chemical Society·Erica L IngallsForrest E Michael
Jul 24, 2013·Chemistry : a European Journal·Timothy W Liwosz, Sherry R Chemler
Oct 11, 2013·Journal of the American Chemical Society·Ryan W EvansDavid W C MacMillan
Dec 24, 2013·The Journal of Organic Chemistry·Gerardo X OrtizQiu Wang
Mar 5, 2014·Organic Letters·Bo Zhang, Armido Studer
Jun 17, 2014·Chemical Science·Benjamin W Turnpenny, Sherry R Chemler
Sep 19, 2014·Journal of the American Chemical Society·David E OlsonJ Du Bois
Nov 18, 2014·Accounts of Chemical Research·Yingguang ZhuYian Shi
Jan 8, 2015·Journal of Medicinal Chemistry·Arun K Ghosh, Margherita Brindisi
Feb 13, 2015·Accounts of Chemical Research·Johan CornilJanine Cossy
May 24, 2015·Bioorganic & Medicinal Chemistry·Kamil KokoszaDorota G Piotrowska
Feb 9, 2016·Journal of the American Chemical Society·Joyann S BarberNeil K Garg
Dec 17, 2016·Chemical Reviews·Mathéo BerthetJean Martinez
Mar 10, 2017·Journal of the American Chemical Society·Kilian MuñizClaudio Martínez
Jul 1, 2015·Chemical Science·Kun Shen, Qiu Wang

❮ Previous
Next ❯

Citations

Sep 24, 2020·Organic & Biomolecular Chemistry·Shuang YangZhenhua Ding
Mar 19, 2021·Organic & Biomolecular Chemistry·Ziying WuHuanfeng Jiang
May 16, 2019·The Journal of Organic Chemistry·Lin Wang, Chuan Wang
May 1, 2018·The Journal of Organic Chemistry·Justin Y SuJ Du Bois

❮ 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.