Zirconium-catalyzed enantioselective [3+2] cycloaddition of hydrazones to olefins leading to optically active pyrazolidine, pyrazoline, and 1,3-diamine derivatives

Journal of the American Chemical Society
Yasuhiro Yamashita, Shū Kobayashi

Abstract

Asymmetric [3+2] cycloaddition of hydrazones to external olefins has been successfully conducted in high yields with high enantioselectivities using a chiral zirconium catalyst. These reactions open ways to synthetically and biologically important pyrazoline, pyrazolidine, and 1,3-diamine derivatives. Further, several experiments suggested that the reactions proceeded via concerted pathways.

References

Sep 1, 1996·Stroke; a Journal of Cerebral Circulation·K UmemuraM Nakashima
Jan 5, 2000·European Journal of Pharmacology·F ShimadaN Saito
Jun 29, 2001·Organic Letters·M Sugiura, S Kobayashi
Nov 15, 2002·Journal of the American Chemical Society·Shū KobayashiJun Kobayashi
May 29, 2003·Journal of the American Chemical Society·Shū KobayashiMasaharu Sugiura
Jun 24, 2004·Journal of the American Chemical Society·Tomoaki HamadaShu Kobayashi

❮ Previous
Next ❯

Citations

Mar 5, 2010·Journal of the American Chemical Society·Takuya HashimotoKeiji Maruoka
Jul 23, 2013·Journal of the American Chemical Society·Takuya HashimotoKeiji Maruoka
Aug 14, 2013·Organic Letters·Mingxin ChangXumu Zhang
Feb 18, 2016·Chemical Reviews·Liang HongRui Wang
May 20, 2016·Organic Letters·Zhang-Pei ChenYong-Gui Zhou
Oct 27, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wei-Min Chen
Jul 4, 2015·Organic & Biomolecular Chemistry·Carmen NájeraMiguel Yus
Jul 14, 2017·Organic & Biomolecular Chemistry·Xiansha PengYulai Hu
Dec 22, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Franc PožganBogdan Štefane
Nov 28, 2009·Angewandte Chemie·Steffen Müller, Benjamin List
Aug 18, 2010·Angewandte Chemie·Olivier MahéJean-François Brière
Apr 28, 2007·Organic & Biomolecular Chemistry·Kazutaka SekiShū Kobayashi
Nov 2, 2011·Beilstein Journal of Organic Chemistry·Aurélie Dos SantosCaroline Ronsseray
Jul 6, 2017·Acta Crystallographica. Section C, Structural Chemistry·Philipp Kramer, Michael Bolte
Apr 26, 2012·Advanced Synthesis & Catalysis·Chengfeng JingHongchao Guo
Apr 13, 2012·Organic & Biomolecular Chemistry·Olivier MahéJean-François Brière
May 25, 2010·Chemistry : a European Journal·Florian JakobThorsten Bach
Jun 1, 2012·ChemistryOpen·Luca DeianaArmando Córdova
May 12, 2015·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka

❮ 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.