PMID: 11925215Apr 2, 2002Paper

Asymmetric N1 unit transfer to olefins with a chiral nitridomanganese complex: novel stereoselective pathways to aziridines or oxazolines

The Journal of Organic Chemistry
Masaaki NishimuraMitsuo Komatsu

Abstract

Chiral nitridomanganese complex 1 was found to be a highly potential N1 unit source for the asymmetric synthesis of aziridines and 2-oxazolines from olefins such as styrene and its derivatives. When sulfonyl chlorides were employed as activators of the complex in the presence of pyridine, pyridine N-oxide, and a silver salt, the reaction of olefins with complex 1 proceeded smoothly to afford the N-sulfonylated aziridines. The aziridination of styrene derivatives with complex 1 using 2-trimethylsilylethanesulfonyl chloride (SESCl) gave the N-SES-aziridines, which were easily converted into chiral N-unsubstituted aziridines. It was found that the reaction was applicable to the asymmetric synthesis of 2-oxazolines from olefins when acyl chlorides were employed as activators. Complex 1 provided an effective asymmetric environment for trans-disubstituted styrenes in the reaction (up to 92% ee). This is the first example of a direct asymmetric synthesis of 2-oxazolines from olefins. Additional experiments, conducted during the course of this investigation, suggest that the isomerization of the N-acylaziridine intermediate is involved in this reaction.

References

May 1, 1976·Chemical & Pharmaceutical Bulletin·M TomieN Yoneda
Jul 13, 2000·Accounts of Chemical Research·G Helmchen, A Pfaltz
Jul 9, 1999·The Journal of Organic Chemistry·Philippe Dauban, Robert H Dodd

❮ Previous
Next ❯

Citations

Aug 3, 2006·Chemical Communications : Chem Comm·Satoshi MinakataMitsuo Komatsu
Aug 2, 2007·Chemical Communications : Chem Comm·Satoshi MinakataMitsuo Komatsu
Nov 26, 2008·Chemical Communications : Chem Comm·Agathe C MayerCarsten Bolm
Jul 12, 2016·ACS Catalysis·Molly PunkJeremy B Morgan
Feb 19, 2005·Angewandte Chemie·Diego J Ramón, Miguel Yus
Jan 23, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Tatsuya Uchida, Tsutomu Katsuki
Feb 11, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xin ZhouZhanbin Zhang
Oct 28, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anton V KuzminBagrat A Shainyan
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hsin-Yi HungTian-Shung Wu
Aug 11, 2021·Journal of the American Chemical Society·Emily M MumfordScott E Denmark
Oct 13, 2011·Organic Letters·Anil K GuptaWilliam D Wulff
Apr 29, 2011·Journal of the American Chemical Society·Ryoichi KuwanoRyuhei Ikeda
Sep 17, 2011·Organic Letters·Hélène LebelMichaël Parmentier
Apr 17, 2019·The Journal of Organic Chemistry·Peter BellottiEtienne Brachet
Jun 15, 2006·Chemical Reviews·Patrice RibièreFrédéric Lamaty
Apr 12, 2003·The Journal of Organic Chemistry·Takayuki TsuritaniKoichiro Oshima

❮ Previous
Next ❯

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.