Directed C-C bond cleavage of a cyclopropane intermediate generated from N-tosylhydrazones and stable enaminones: expedient synthesis of functionalized 1,4-ketoaldehydes

Chemical Communications : Chem Comm
Meiyan NiTeck-Peng Loh

Abstract

An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from N-tosylhydrazones, followed by selective C-C bond cleavage of the cyclopropane ring, affords 1,4-ketoaldehyde derivatives in good to excellent yields. This method works with broad substrate scope and high regioselectivity.

References

May 18, 2000·The Journal of Organic Chemistry·M SonoM Tori
Apr 30, 2002·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Sean S DaviesL Jackson Roberts
Jun 23, 2005·Journal of the American Chemical Society·Zhuo TangLiu-Zhu Gong
Aug 3, 2006·Journal of the American Chemical Society·Manabu HatanoKazuaki Ishihara
Aug 15, 2006·Angewandte Chemie·Zhe GengPauline Chiu
Sep 30, 2006·Angewandte Chemie·Phil S Baran, Michael P DeMartino
May 15, 2007·Journal of the American Chemical Society·Hye-Young JangDavid W C MacMillan
Aug 6, 2008·Journal of the American Chemical Society·Michael P DeMartinoPhil S Baran
Apr 3, 2009·Journal of the American Chemical Society·Ryan A Shenvi, E J Corey
Jun 9, 2009·Chemical Communications : Chem Comm·Hai ZhouTeck-Peng Loh
Aug 28, 2009·Journal of Natural Products·Xiaomei ChenJunshan Yang
Jan 1, 2010·Chemical Research in Toxicology·Irene Zagol-IkapitteOlivier Boutaud
Jan 30, 2010·Science·Mark S Chen, M Christina White
Mar 23, 2010·Journal of the American Chemical Society·De-Jun DongShi-Kai Tian
May 18, 2010·Free Radical Biology & Medicine·Irina G StavrovskayaBruce S Kristal
Feb 11, 2012·Chemical Communications : Chem Comm·Yaojia JiangCheol-Min Park
Apr 21, 2012·Angewandte Chemie·Sreekumar PankajakshanTeck-Peng Loh
Mar 27, 2013·Organic Letters·Bibhuti Bhusan ParidaJin Kun Cha
Apr 16, 2014·Journal of the American Chemical Society·Kah Kah TohShunsuke Chiba
Mar 10, 2015·Journal of the American Chemical Society·Xiaomin Xie, Shannon S Stahl
Mar 24, 2015·Journal of the American Chemical Society·Hirotsugu SuzukiShū Kobayashi
Mar 31, 2015·Chemical Communications : Chem Comm·Pan XuChengjian Zhu
Dec 15, 2015·Organic Letters·Hongbo WeiHongbin Zhai
May 11, 2016·The Journal of Organic Chemistry·Keshab MondalSubhas Chandra Pan

❮ Previous
Next ❯

Citations

Jul 7, 2019·Angewandte Chemie·Jie ChenTeck-Peng Loh
Jan 23, 2020·Chemical Communications : Chem Comm·Xiaoyu LiangYaojia Jiang
Aug 19, 2020·Chemical Communications : Chem Comm·Mingrui LiHe Huang
May 14, 2021·Chemical Communications : Chem Comm·Chengzhou JiangYaojia Jiang
May 28, 2021·The Journal of Organic Chemistry·Andriy I FrolovSergey V Ryabukhin
Oct 11, 2019·The Journal of Organic Chemistry·Chun-Ying WangXiang-Ying Tang
Feb 9, 2018·Organic Letters·Fei WangTeck-Peng Loh

❮ Previous
Next ❯

Methods Mentioned

BETA
acylation
NMR
X-ray

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.