Catalytic Regio- and Enantioselective Alkylation of Conjugated Dienyl Amides

Angewandte Chemie
Yafei GuoSyuzanna R Harutyunyan

Abstract

A method for catalytic asymmetric alkylation of conjugated dienyl amides has been developed and it allows efficient and high-yielding transformations of a wide range of polyconjugated amides into the corresponding chiral products. Smooth addition of organomagnesium reagents to relatively unreactive dienyl amides with excellent 1,6- and 1,4-selectivities, as well as enantioselectivites above 90 %, is achieved owing to the complementary action of the Lewis acid and a chiral copper-based catalyst.

References

Nov 15, 2006·Angewandte Chemie·Bernd Schetter, Rainer Mahrwald
Apr 19, 2007·Chemistry, an Asian Journal·Naohiko YoshikaiEiichi Nakamura
Nov 29, 2007·Angewandte Chemie·Tim den HartogBen L Feringa
Aug 14, 2008·Chemical Reviews·Syuzanna R HarutyunyanBen L Feringa
Oct 18, 2008·Angewandte Chemie·Hélène HénonAlexandre Alexakis
May 21, 2010·Journal of the American Chemical Society·Takahiro NishimuraTamio Hayashi
Jul 30, 2010·Chemical Society Reviews·Aurelio G CsákÿM Carmen Murcia
Sep 3, 2010·Organic Letters·Joanna Wencel-DelordMarc Mauduit
Apr 21, 2012·Chemical Science·Anna E Allen, David W C Macmillan
Nov 8, 2012·Journal of the American Chemical Society·Takahiro SawanoTamio Hayashi
Nov 14, 2012·Journal of the American Chemical Society·Daisuke UraguchiTakashi Ooi
Nov 19, 2014·Angewandte Chemie·Jiawei RongSyuzanna R Harutyunyan
Sep 30, 2017·Journal of the American Chemical Society·Mamen Rodríguez-FernándezSyuzanna R Harutyunyan
Jan 6, 2018·Journal of the American Chemical Society·Liang WeiChun-Jiang Wang

❮ Previous
Next ❯

Citations

Mar 18, 2020·Beilstein Journal of Organic Chemistry·Delphine PichonMarc Mauduit
Nov 1, 2020·Nature Communications·Chang-Yun ShiLiang Yin
Sep 23, 2020·Chemistry : a European Journal·Kirill KulishSyuzanna R Harutyunyan
Jul 14, 2021·Journal of the American Chemical Society·Christopher J C CoozeRylan J Lundgren
Jan 30, 2019·Organic Letters·Pengfei ZhouXiaoming Feng
Feb 1, 2022·Organic Letters·Aitor MaestroSyuzanna R Harutyunyan

❮ 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.