Chiral phosphoric acid catalyzed enantioselective decarboxylative alkylation of β-keto acids with 3-hydroxy-3-indolyloxindoles

Organic Letters
Xiao-Dong TangJun-An Ma

Abstract

A chiral phosphoric acid catalyzed enantioselective decarboxylative alkylation of β-keto acids with 3-hydroxy-3-indolyloxindoles is described in this context. This method tolerates a series of aromatic and aliphatic β-keto acids as well as substituted 3-hydroxy-3-indolyloxindoles, affording the corresponding chiral 3-functionalized 3-indolyloxindoles in high yields (up to 98%) and enantioselectivities (up to 99% ee).

References

Oct 24, 2001·The Journal of Organic Chemistry·Mustafa VarogluPhillip Crews
Dec 28, 2006·Journal of Natural Products·Chang-Ji ZhengWon-Gon Kim
Nov 7, 2007·Chemical Reviews·Takahiko Akiyama
Dec 13, 2007·Chemical Reviews·Abigail G Doyle, Eric N Jacobsen
Feb 21, 2008·Chemistry, an Asian Journal·Xinhong Yu, Wei Wang
Dec 24, 2009·Angewandte Chemie·Nadine V HanhanAnnaliese K Franz
Mar 6, 2010·Organic & Biomolecular Chemistry·Alessandro PalmieriRafik R Shaikh
Jan 27, 2011·Chemistry : a European Journal·Pau Ruiz-SanchisMercedes Álvarez
Mar 9, 2011·Organic Letters·Kerstin Rohr, Rainer Mahrwald
May 27, 2011·Chemical Society Reviews·Magnus RuepingIuliana Atodiresei
Jan 21, 2012·Angewandte Chemie·Liu SongYun-Gui Peng
Mar 2, 2012·Organic & Biomolecular Chemistry·Luca BernardiAlfredo Ricci
Aug 18, 2012·Chemical Society Reviews·Renato DalpozzoGiorgio Bencivenni
Nov 15, 2012·Chemical Communications : Chem Comm·Jian Lv, Sanzhong Luo
Feb 19, 2013·Organic & Biomolecular Chemistry·Ying ZhangShun-Jun Ji
Nov 26, 2013·Organic & Biomolecular Chemistry·Shuichi Nakamura

❮ Previous
Next ❯

Citations

Sep 25, 2015·The Journal of Organic Chemistry·Ming DingChengfeng Xia
May 20, 2017·Chemical Communications : Chem Comm·Tonghao Zhu, Shengming Ma
Jul 15, 2017·The Journal of Organic Chemistry·Guang-Jian Mei, Feng Shi
May 19, 2018·Organic & Biomolecular Chemistry·Man-Yi HanLei Wang
Jun 25, 2016·Beilstein Journal of Organic Chemistry·Bin YuHong-Min Liu

❮ 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.