Direct Catalytic Enantioselective Vinylogous Aldol Reaction of Allyl Ketones to Pyrazole-4,5-diones

The Journal of Organic Chemistry
Bidisha Ray, Santanu Mukherjee

Abstract

The first catalytic enantioselective vinylogous nucleophilic addition to pyrazole-4,5-diones is reported. Using quinine-derived bifunctional tertiary amino-amide as the catalyst, this direct aldol reaction of allyl ketones is shown to proceed exclusively in γ- and E-selective manner to generate pyrazolone derivatives, bearing an oxygen-containing quaternary stereogenic center, in good yields with moderate to high enantioselectivities (up to 97:3 er).

References

Oct 16, 2003·Journal of the American Chemical Society·Tomotaka OkinoYoshiji Takemoto
May 14, 2004·Journal of Medicinal Chemistry·Michael P ClarkMichael J Janusz
Jun 9, 2005·Angewandte Chemie·Scott E DenmarkGregory L Beutner
Jun 23, 2005·Journal of the American Chemical Society·Douglas E Fuerst, Eric N Jacobsen
May 29, 2008·Chemical Communications : Chem Comm·Stephen J Connon
Oct 23, 2009·Chemical Society Reviews·Timothy NewhouseReinhard W Hoffmann
Sep 25, 2010·Bioorganic & Medicinal Chemistry Letters·Victor HadiKyung Woon Jung
Mar 26, 2011·Chemical Reviews·Giovanni CasiraghiFranca Zanardi
Aug 4, 2012·Organic & Biomolecular Chemistry·Abhijnan Ray Choudhury, Santanu Mukherjee
Oct 19, 2012·Organic Letters·Carlo Cassani, Paolo Melchiorre
Jul 5, 2013·Angewandte Chemie·Chandra Bhushan Tripathi, Santanu Mukherjee
Jul 25, 2013·Angewandte Chemie·Jun-ichi Matsuo, Masahiro Murakami
Oct 23, 2013·Chemical Communications : Chem Comm·Qian ShaoYong Huang
Nov 23, 2013·Organic & Biomolecular Chemistry·Ivan Franzoni, Clément Mazet
Apr 11, 2014·Nature·Tian-Sheng MeiMatthew S Sigman
Apr 25, 2014·Organic & Biomolecular Chemistry·Christoph Schneider, Falko Abels
Jun 2, 2015·Journal of the American Chemical Society·Chun ZhangMatthew S Sigman
Jul 17, 2015·Chemical Communications : Chem Comm·Pankaj ChauhanDieter Enders
Dec 10, 2015·Organic & Biomolecular Chemistry·Amit K Simlandy, Santanu Mukherjee
Feb 20, 2016·Nature Chemistry·Alexandre VasseurIlan Marek
Sep 8, 2016·Chemistry : a European Journal·Madhu Sudan MannaSantanu Mukherjee
Oct 7, 2016·Chemical Communications : Chem Comm·Xiaoze BaoBaomin Wang
Feb 1, 2017·Journal of the American Chemical Society·Hai-Jun ZhangLiang Yin
May 26, 2017·The Journal of Organic Chemistry·Pankaj ChauhanDieter Enders
Jun 7, 2017·Chemical Communications : Chem Comm·Suruchi MahajanDieter Enders
Jul 29, 2017·Organic & Biomolecular Chemistry·Soumya Jyoti Singha Roy, Santanu Mukherjee
Apr 18, 2018·Journal of the American Chemical Society·Harshkumar H PatelMatthew S Sigman

❮ Previous
Next ❯

Citations

May 16, 2019·Chemistry : a European Journal·Iñaki UrruzunoClaudio Palomo
Sep 10, 2019·Chemical Communications : Chem Comm·Jian LuXin-Yan Wu
Feb 23, 2020·Organic & Biomolecular Chemistry·Prakash K WarghudeRamakrishna G Bhat
Nov 22, 2020·Angewandte Chemie·Si-Qing WangLiang Yin
Jan 17, 2021·Chemistry : a European Journal·Rong-Hui WangFen-Er Chen
May 8, 2021·Chemistry : a European Journal·Mikel Oiarbide, Claudio Palomo

❮ 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.