Trisoxazoline/Cu(II)-promoted Kinugasa reaction. Enantioselective synthesis of beta-lactams

The Journal of Organic Chemistry
Meng-Chun YeYong Tang

Abstract

The reactions of nitrones with terminal alkynes, catalyzed by chiral (i)Pr-trisoxazoline 2a/Cu(ClO4)2.6H2O under air atmosphere, afforded beta-lactams in moderate to good yields with up to 85% ee. The diastereoselectivity depends on the alkyne. Propiolate gives the trans-isomer as a major product, while the other alkynes afford cis-disubstituted lactams predominantly. Copper(II) salt proved to be an efficient catalyst precursor for the first time in the Kinugasa reaction, and this allowed the reaction to be performed under a practical and convenient condition. An appropriate base used in this reaction was essential to control both diastereoselectivity and enantioselectivity. Compared with primary and tertiary amines, secondary amines gave higher enantioselectivities. The reaction scope and limitation as well as the mechanism were also studied.

References

Sep 26, 2002·Angewandte Chemie·Stéphane Bellemin-Laponnaz, Lutz H Gade
Jun 6, 2003·Journal of the American Chemical Society·Thomas F Knöpfel, Erick M Carreira
Apr 27, 2004·Angewandte Chemie·José Marco-Contelles
May 11, 2004·Journal of Combinatorial Chemistry·Jian ZhouYong Tang
Dec 17, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·Markus SeitzLutz H Gade

❮ Previous
Next ❯

Citations

Nov 15, 2011·Chemical Reviews·Giovanni DesimoniKarl Anker Jørgensen
Nov 26, 2015·The Journal of Organic Chemistry·Kamil KabalaMarek Chmielewski
Jan 16, 2009·Angewandte Chemie·David TejedorFernando García-Tellado
Sep 12, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Devaborniny ParasarH V Rasika Dias
Apr 12, 2013·Chemistry : a European Journal·Zhenling ChenXiaoming Feng
Mar 13, 2014·Chemistry : a European Journal·Boris D ZlatopolskiyBernd Neumaier
Jul 23, 2013·Chemistry : a European Journal·Beatriz BaezaMiguel A Sierra
Jun 13, 2014·Chemistry : a European Journal·Mutsuyo OharaShuichi Nakamura
Mar 27, 2020·Organic & Biomolecular Chemistry·Oskar PopikMarek Chmielewski
Aug 9, 2008·The Journal of Organic Chemistry·Sebastian SteckoMarek Chmielewski
Sep 11, 2008·Chemical Reviews·Alberto BrandiFranca M Cordero
Apr 22, 2009·Chemical Reviews·Gráinne C Hargaden, Patrick J Guiry
Mar 28, 2009·The Journal of Organic Chemistry·Sebastian SteckoMarek Chmielewski
Jul 11, 2008·Chemical Reviews·Levi M Stanley, Mukund P Sibi
Jul 14, 2021·The Journal of Organic Chemistry·Stefano Santoro, Fahmi Himo
Mar 20, 2010·Chemical Reviews·Renato DalpozzoPaolo Melchiorre
Feb 6, 2015·The Journal of Organic Chemistry·Stefano SantoroFahmi Himo
Feb 22, 2014·Chemical Reviews·Cody Ross Pitts, Thomas Lectka
May 12, 2015·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka
Jul 3, 2018·Journal of the American Chemical Society·Thomas C MaligJason E Hein
Jul 13, 2011·The Journal of Organic Chemistry·Michał MichalakMarek Chmielewski

❮ 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.

Related Papers

The Journal of Organic Chemistry
Sebastian SteckoMarek Chmielewski
The Journal of Organic Chemistry
Sebastian SteckoMarek Chmielewski
Clinical Cancer Research : an Official Journal of the American Association for Cancer Research
Leeanne J MeadMelissa C Southey
© 2022 Meta ULC. All rights reserved