Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles.

Organic Letters
Joanne E RedfordShannon S Stahl

Abstract

Palladium(II)-catalyzed aerobic oxidative cyclization of alkenes with tethered tert-butanesulfinamides furnishes enantiopure 2,5-disubstituted pyrrolidines, originating from readily available and easily diversified starting materials. These reactions are the first reported examples of metal-catalyzed addition of sulfinamide nucleophiles to alkenes.

References

Nov 10, 2000·Natural Product Reports·D O'Hagan
May 31, 1996·The Journal of Organic Chemistry·Richard C. LarockKarl P. Peterson
Dec 4, 2003·Journal of the American Chemical Society·Sukwon HongTobin J Marks
May 13, 2004·Chemical Reviews·Gilson Zeni, Richard C Larock
Sep 10, 2004·Organic Letters·Douglas M Mans, William H Pearson
May 27, 2005·Organic & Biomolecular Chemistry·Kristin M Brinner, Jonathan A Ellman
Jun 23, 2006·Organic & Biomolecular Chemistry·Syed Raziullah Hussaini, Mark G Moloney
Oct 10, 2006·Angewandte Chemie·Mark C WoodLaurel L Schafer
Apr 19, 2007·Journal of the American Chemical Society·Guosheng Liu, Shannon S Stahl
Jun 20, 2007·Chemical Society Reviews·Ana Minatti, Kilian Muñiz
Nov 2, 2007·Chemical Reviews·Egle M BeccalliSilvia Sottocornola
Dec 4, 2008·Journal of the American Chemical Society·Peter H FullerSherry R Chemler
Dec 17, 2009·Angewandte Chemie·Xiaoqiang Shen, Stephen L Buchwald
Mar 6, 2010·The Journal of Organic Chemistry·Leleti Rajender ReddyMahavir Prashad
Apr 28, 2010·Chemical Reviews·MaryAnn T RobakJonathan A Ellman
Mar 12, 2011·The Journal of Organic Chemistry·Guolin ChengYuefei Hu
Aug 25, 2011·Journal of the American Chemical Society·Jessica M Hoover, Shannon S Stahl

❮ Previous
Next ❯

Citations

Feb 16, 2017·Chemical Communications : Chem Comm·Ana SirventMiguel Yus
May 9, 2015·Chemical Society Reviews·Gellért SiposReto Dorta
Nov 8, 2014·Chemistry : a European Journal·Pavel Kočovský, Jan-E Bäckvall
Oct 13, 2017·Angewandte Chemie·Diana A IovanTheodore A Betley
Jun 8, 2021·Beilstein Journal of Organic Chemistry·Joseane A MendesCamilla D Buarque
Aug 18, 2021·The Journal of Organic Chemistry·Chun-Tai HungCheng-Che Tsai
Oct 5, 2017·Chemical Reviews·Dian WangShannon S Stahl
Dec 15, 2016·Journal of the American Chemical Society·Lin HuLi Deng
Jan 14, 2020·Organic Letters·Anand H Shinde, Shyam Sathyamoorthi

❮ 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.