Copper-Catalyzed Asymmetric Conjugate Additions of Bis(pinacolato)diboron and Dimethylzinc to Acyl- N-methylimidazole Michael Acceptors: A Highly Stereoselective Unified Strategy for 1,3,5,... n (OH, Me) Motif Synthesis

Organic Letters
Jimmy LauberteauxJean-Marc Campagne

Abstract

A unified strategy for the construction of prevalent 1,3,5,... n (OH, Me) motifs based on consecutive copper-catalyzed asymmetric conjugate borylation (ACB) and methylation (ACA) reactions involving α,β-unsaturated 2-acyl- N-methylimidazoles is described. Good yields and high diastereoselectivities have been obtained in ACA and ACB reactions for both matched and mismatched pairs as illustrated in the synthesis of syn/ anti and anti/ anti (Me, OTBS, Me) and (OH, OTBS, Me) motifs.

References

Jul 31, 2007·Journal of the American Chemical Society·David A EvansRisheng Xu
Oct 10, 2007·Angewandte Chemie·Ji-Eon Lee, Jaesook Yun
Jan 10, 2009·Chemistry : a European Journal·Hak-Suk SimJaesook Yun
Jun 11, 2009·Angewandte Chemie·Christian Hertweck
Apr 23, 2010·Chemical Society Reviews·Arnold J BoersmaGerard Roelfes
May 8, 2010·Chemical Communications : Chem Comm·Bjorn ter HorstAdriaan J Minnaard
May 18, 2011·Chemical Communications : Chem Comm·Abraham L MoureJuan C Carretero
Oct 19, 2011·Angewandte Chemie·Ismail IbrahemArmando Córdova
Apr 18, 2012·Organic Letters·Eduard Hartmann, Martin Oestreich
Jul 31, 2013·Natural Product Reports·Melvin J YuBoris M Seletsky
Jan 28, 2015·Journal of the American Chemical Society·Sebastien BalieuVarinder K Aggarwal
Jun 9, 2015·Frontiers in Chemistry·Kuan ZhengRan Hong
Feb 26, 2016·Proceedings of the National Academy of Sciences of the United States of America·Yusuke OtaKyoko Nozaki
Jul 20, 2016·Chemical Reviews·Emily C NeeveTodd B Marder
Jan 28, 2017·Accounts of Chemical Research·Lilu Zhang, Eric Meggers
Sep 13, 2018·Chemical Society Reviews·David HemmingPatrick G Steel

❮ Previous
Next ❯

Citations


❮ 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.