Gold-catalyzed highly enantioselective synthesis of axially chiral allenes.

Organic Letters
Vanessa Kar-Yan LoChi-Ming Che

Abstract

Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4 in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 degrees C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(I)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture.

References

Aug 31, 2002·Angewandte Chemie·Anja Hoffmann-Röder, Norbert Krause
May 13, 2004·Journal of the American Chemical Society·Hiroyuki NakamuraJean-François Biellmann
Dec 9, 2004·Journal of the American Chemical Society·Benjamin D Sherry, F Dean Toste
Jan 29, 2005·Organic & Biomolecular Chemistry·Anja Hoffmann-Röder, Norbert Krause
Nov 1, 2005·Angewandte Chemie·A Stephen K Hashmi
Dec 13, 2005·Angewandte Chemie·Shengming MaZhenhua Gu
Jan 18, 2006·Organic Letters·Cong-Ying ZhouChi-Ming Che
Nov 30, 2006·Angewandte Chemie·A Stephen K Hashmi, Graham J Hutchings
Mar 10, 2007·Angewandte Chemie·Nicolas Marion, Steven P Nolan
Mar 23, 2007·Nature·David J Gorin, F Dean Toste
Jun 22, 2007·Chemical Reviews·A Stephen K Hashmi
Aug 19, 2007·Proceedings of the National Academy of Sciences of the United States of America·Vincent LavalloGuy Bertrand
Dec 1, 2000·Angewandte Chemie·Gerald Dyker

❮ Previous
Next ❯

Citations

Jul 26, 2008·Journal of the American Chemical Society·Xiaotao Pu, Joseph M Ready
May 6, 2010·Chemical Communications : Chem Comm·Li CuiLiming Zhang
Oct 29, 2010·Chemical Communications : Chem Comm·Pierrick NunSteven P Nolan
Mar 17, 2011·Chemical Communications : Chem Comm·Shichao Yu, Shengming Ma
Jan 5, 2016·Organic Letters·Chunliang ZhaoWei He
Mar 27, 2015·Chemical Communications : Chem Comm·G GangadhararaoK C Kumara Swamy
Jul 13, 2017·The Journal of Organic Chemistry·Maren Schaarschmidt, Klaus T Wanner
Aug 31, 2016·Topics in Current Chemistry·Liang Wang, Jian Xiao
May 23, 2015·Organic & Biomolecular Chemistry·Vanessa Kar-Yan LoChi-Ming Che
Sep 18, 2013·Nature Communications·Xinjun TangShengming Ma
Mar 6, 2015·Organic & Biomolecular Chemistry·Jiasheng ZhangShengming Ma
Jun 20, 2018·Angewandte Chemie·Pernille H PoulsenKarl Anker Jørgensen
Jun 8, 2012·Chemistry, an Asian Journal·Nitin T Patil
Aug 22, 2013·Chemical Communications : Chem Comm·Xinjun TangShengming Ma
Sep 13, 2013·Chemistry : a European Journal·Bo Peng, Nuno Maulide
Mar 22, 2012·Chemical Communications : Chem Comm·Gai-Li LiMan-Kin Wong
Sep 21, 2013·Chemical Communications : Chem Comm·Wu Fan, Shengming Ma
Nov 13, 2012·Chemistry : a European Journal·Juntao YeShengming Ma
Jun 9, 2016·Angewandte Chemie·Aurélien TapBenjamin List
Apr 8, 2014·Angewandte Chemie·Michael C Haibach, Daniel Seidel
Jan 17, 2013·Chemical Communications : Chem Comm·Anna On-Yee ChanChi-Ming Che
Sep 11, 2012·Angewandte Chemie·Baoqiang Wan, Shengming Ma
Jun 6, 2009·Journal of the American Chemical Society·Li CuiLiming Zhang
Jan 28, 2010·Journal of the American Chemical Society·Jinqiang Kuang, Shengming Ma
Feb 18, 2010·Journal of the American Chemical Society·Igor Dias JurbergFabien Gagosz
Aug 31, 2011·Journal of the American Chemical Society·Weidong RaoPhilip Wai Hong Chan
Mar 12, 2011·Chemical Reviews·Corinne AubertAntoine Simonneau

❮ 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.