Catalyst-Free Ring Opening of Spiroaziridine Oxindoles by Heteronucleophiles: An Approach to the Synthesis of Enantiopure 3-Substituted Oxindoles

The Journal of Organic Chemistry
Saumen HajraSk Abu Saleh

Abstract

A simple catalyst-free method was developed for the ring opening of spiroaziridine oxindoles by three different nucleophiles, namely, amines, thiols, and methanol, to produce enantiopure (up to 99%) vicinal diaminooxindoles, β-aminosulfides, and β-amino-3-methoxyoxindole, respectively, in good to excellent yields. In contrast to the spiroepoxides, spiroaziridines are opened regio- and stereospecifically through the pseudobenzylic spirocenter under catalyst-free conditions. Moreover, unlike simple 2-substituted aziridines, these spiroaziridines are opened up with retention in configuration at the C3-spirocenter.

References

Nov 6, 2002·Proceedings of the National Academy of Sciences of the United States of America·Masahiko HayashiSatoshi Omura
Aug 14, 2003·Chemical Reviews·Amy B Dounay, Larry E Overman
Dec 25, 2003·Angewandte Chemie·Satoshi MinakataMitsuo Komatsu
May 20, 2004·Journal of the American Chemical Society·Songnian LinSamuel J Danishefsky
Dec 21, 2006·Journal of the American Chemical Society·Takehisa IshimaruShuji Kanemasa
Mar 29, 2007·Journal of the American Chemical Society·Yousung Jung, R A Marcus
Feb 22, 2008·The Journal of Organic Chemistry·Matteo CalvaresiMarco Garavelli
Jul 18, 2008·The Journal of Organic Chemistry·Nicolas ProustLeo A Paquette
Sep 2, 2008·Chemical Communications : Chem Comm·Yi-Xia JiaE Peter Kündig
Aug 28, 2009·Organic Letters·Liang ChengYong-Jun Chen
Feb 16, 2011·Chemical Communications : Chem Comm·Saumen Hajra, Sukanta Bar
Sep 7, 2011·Chemical Society Reviews·Sonja StankovićHyun-Joon Ha
Nov 25, 2011·Organic & Biomolecular Chemistry·Xavier CompanyóRamon Rios
Sep 7, 2012·Chemical Reviews·Girija S Singh, Zelalem Y Desta
Nov 21, 2012·Angewandte Chemie·Mani Sengoden, Tharmalingam Punniyamurthy
Jan 11, 2013·Chemical Communications : Chem Comm·Jianhao LiYungui Peng
Mar 29, 2014·Angewandte Chemie·Tomohiko ShiraiYasunori Yamamoto
Apr 6, 2017·Chemical Communications : Chem Comm·Imtiyaz Ahmad WaniManas K Ghorai

❮ Previous
Next ❯

Citations

Oct 13, 2020·Organic & Biomolecular Chemistry·Akash P SaklaNagula Shankaraiah
Mar 23, 2021·Chemistry : a European Journal·Wenkun YangXiaoming Feng
Jun 9, 2021·Organic & Biomolecular Chemistry·Anurag BiswasSaumen Hajra
Jun 25, 2021·Chemical Science·Xuan WangXiaojie Lu
Jul 24, 2018·Organic Letters·Saumen HajraSk Abu Saleh

❮ 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.