Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles

Chemical Science
Yu-Long HuLing Zhou

Abstract

Central-to-axial chirality conversion provides efficient access to axially chiral compounds, and several examples regarding the conversion of one, two or four stereocenters to one axis have been reported. Herein, we report the conversion of two stereocenters to one or two chiral axes for the first time. In this study, a new class of enantiomerically enriched 2,3-diarylbenzoindoles was efficiently synthesized using a chiral phosphoric acid-catalyzed [3 + 2] formal cycloaddition and a mild DDQ oxidation strategy. Moreover, a speculative model of the central-to-axial chirality conversion outcome was proposed based on preliminary mechanistic studies and DFT calculations. Potentially, using this strategy, useful chiral phosphine ligand can be synthesized smoothly (99% ee).

References

Jun 6, 2002·Journal of the American Chemical Society·Andrei V VorogushinHans-Jürgen Hansen
Nov 7, 2002·Journal of the American Chemical Society·Toyoshi ShimadaTamio Hayashi
Aug 14, 2003·Chemical Reviews·Wenjun Tang, Xumu Zhang
Aug 14, 2003·Chemical Reviews·Pavel KocovskýMartin Smrcina
Jul 12, 2008·Angewandte Chemie·Chau Ming SoFuk Yee Kwong
Sep 12, 2008·The Journal of Organic Chemistry·Chau Ming SoFuk Yee Kwong
Sep 13, 2008·Angewandte Chemie·Chau Ming SoFuk Yee Kwong
Oct 23, 2009·Chemical Society Reviews·Marisa C KozlowskiElizabeth C Linton
May 13, 2010·Chemistry : a European Journal·Nobutaka OtotakeOsamu Kitagawa
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Dec 15, 2010·Journal of the American Chemical Society·Fenghai GuoRegan J Thomson
May 11, 2013·Journal of the American Chemical Society·Gong-Qiang LiLászló Kürti
Oct 11, 2013·Journal of the American Chemical Society·Abel RosJosé M Lassaletta
Oct 25, 2013·Journal of the American Chemical Society·Vikram BhatScott C Virgil
Sep 10, 2014·Journal of the American Chemical Society·Xingwei GuoHerbert Mayr
Apr 24, 2015·Chemical Society Reviews·J Wencel-DelordF Colobert
Aug 8, 2015·Nature Communications·Shangze WuShengming Ma
Oct 31, 2015·Angewandte Chemie·Mukesh PappoppulaAaron Aponick
Nov 13, 2015·Journal of the American Chemical Society·Ye-Hui ChenBin Tan
Nov 18, 2015·Angewandte Chemie·Mukesh Pappoppula, Aaron Aponick

❮ Previous
Next ❯

Citations

Mar 24, 2020·Angewandte Chemie·Xiaoze BaoDamien Bonne
Aug 6, 2020·Chemistry, an Asian Journal·Hui YangLing Zhou
May 5, 2020·Chemistry : a European Journal·Tian-Zhen LiFeng Shi
Mar 30, 2021·Chemical Reviews·Jun Kee ChengBin Tan
May 8, 2021·Journal of the American Chemical Society·Qianwen GaoQianghui Zhou
Aug 16, 2019·Organic Letters·Huai-Ri SunLing Zhou
Jul 16, 2020·The Journal of Organic Chemistry·Ke-Wei ChenFeng Shi
Aug 29, 2020·Journal of the American Chemical Society·Omar M BelehScott J Miller

❮ Previous
Next ❯

Methods Mentioned

BETA
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.