H-Bond-Directing Organocatalyst for Enantioselective [4 + 2] Cycloadditions via Dienamine Catalysis

Organic Letters
Shoulei WangMiquel A Pericàs

Abstract

An efficient, highly regio- and stereoselective [4 + 2] cycloaddition reaction to generate tetrahydropyranopyrazole frameworks has been developed. To this end, a dienamine-based catalytic strategy that relies on the H-bond-directing effect of the hydroxy group of a dinaphthylprolinol-type aminocatalyst has been used. This enables the synthesis of multifunctionalized heterocyclic derivatives with three contiguous stereocenters in good yields and excellent enantioselectivities.

References

Sep 28, 2006·Journal of the American Chemical Society·Søren BertelsenKarl Anker Jørgensen
Feb 8, 2008·European Journal of Medicinal Chemistry·Samir BondockAhmed A Fadda
Jun 2, 2009·Bioorganic & Medicinal Chemistry Letters·Kuppusamy SujathaMelani Rajendran
Nov 17, 2009·Tetrahedron Letters·Sanjib Gogoi, Cong-Gui Zhao
Aug 3, 2011·Chemical Reviews·Santos FusteroAntonio Simón-Fuentes
Aug 16, 2011·Organic & Biomolecular Chemistry·Alex ZeaRamon Rios
Jan 13, 2012·Organic & Biomolecular Chemistry·Andrea MazzantiRamon Rios
Jan 28, 2012·Journal of the American Chemical Society·Łukasz AlbrechtKarl Anker Jørgensen
Jun 22, 2012·Accounts of Chemical Research·Jun-Long LiYing-Chun Chen
Jul 24, 2012·Bioorganic & Medicinal Chemistry Letters·Santhosh Reddy MandhaSridhar Balasubramanian
Aug 3, 2012·Organic Letters·Dieter EndersCarina Merkens
Apr 20, 2013·Chemical Communications : Chem Comm·Igor D JurbergPaolo Melchiorre
Aug 14, 2013·Organic & Biomolecular Chemistry·Jun-Hua Li, Da-Ming Du
Dec 7, 2013·Chemistry : a European Journal·Lukasz AlbrechtKarl Anker Jørgensen
Mar 29, 2014·The Journal of Organic Chemistry·Christian F WeiseKarl Anker Jørgensen
Nov 5, 2014·Journal of the American Chemical Society·Lorenzo CaruanaKarl Anker Jørgensen
Jul 17, 2015·Chemical Communications : Chem Comm·Pankaj ChauhanDieter Enders

❮ Previous
Next ❯

Citations

Mar 23, 2018·Chemical Communications : Chem Comm·Taichi KanoKeiji Maruoka
May 25, 2016·Chemical Communications : Chem Comm·Jakob BlomKarl Anker Jørgensen
Oct 7, 2016·Chemical Communications : Chem Comm·Xiaoze BaoBaomin Wang
Sep 19, 2018·Chemical Communications : Chem Comm·Siyuan LiuBaomin Wang
Apr 3, 2016·Chemistry, an Asian Journal·Carlos VilaJosé R Pedro
Mar 8, 2016·Angewandte Chemie·Jagadeesh Kalepu, Sreenivas Katukojvala

❮ 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.