Control of selectivity in the generation and reactions of oxonium ylides

Chemical Communications : Chem Comm
Deana M JaberMichael P Doyle

Abstract

Dirhodium catalyzed reactions of aryl-substituted tetrahydropyranone diazoacetoacetates produce ylide intermediates that unexpectedly yield two oxabicyclo[4.2.1]-nonane diastereoisomers, but a single diastereoisomer is formed by increasing the steric bulk of the aryl substituent.

References

Jul 18, 2001·Journal of the American Chemical Society·F P Marmsäter, F G West
Dec 26, 2001·Chemical Reviews·L Yet
Jan 5, 2002·Journal of the American Chemical Society·Jiang LongKuiling Ding
Mar 27, 2003·Journal of the American Chemical Society·Naoya Shibayama, Satoshi Saigo
Dec 4, 2003·Journal of the American Chemical Society·Fredrik P MarmsäterF G West
Dec 20, 2003·The Journal of Organic Chemistry·Yuichi SawadaAkira Oku
Apr 3, 2004·Proceedings of the National Academy of Sciences of the United States of America·Michael P DoylePenglin Huang
May 7, 2004·Organic Letters·Fredrik P MarmsäterF G West
May 21, 2004·Organic Letters·J Stephen ClarkClaire Wilson
Feb 3, 2005·Journal of the American Chemical Society·Aditya K UnniViresh H Rawal
Sep 14, 2006·Chemical Reviews·Giovanni DesimoniKarl Anker Jørgensen
Dec 6, 2006·Angewandte Chemie·J Stephen ClarkLuca Gobbi
Jul 25, 2007·Angewandte Chemie·John C Jewett, Viresh H Rawal
Jan 4, 2008·The Journal of Organic Chemistry·J Stephen ClarkWilliam G Whittingham
Oct 24, 2008·Chemical Reviews·Sébastien Reymond, Janine Cossy
May 8, 2009·Chemical Society Reviews·J B Sweeney
Aug 19, 2009·Journal of Natural Products·Wei-Lie XiaoHan-Dong Sun

❮ Previous
Next ❯

Citations

Mar 14, 2012·Organic Letters·Deana M JaberMichael P Doyle
Jul 21, 2017·Chemical Society Reviews·Qing-Qing ChengMichael P Doyle
Apr 12, 2012·Chemistry : a European Journal·Rafael Ballesteros-GarridoJérôme Lacour
Mar 22, 2014·Chemistry : a European Journal·J Stephen Clark, K Emelie Hansen
Aug 9, 2020·Angewandte Chemie·Meredith A AllenAndré M Beauchemin

❮ 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.

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.

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.

Epigenetics Insights from Twin Studies

Find the latest research on epigenetics and twin studies 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.

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.

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.

Regulation of Vocal-Motor Plasticity

Dopaminergic projections to the basal ganglia and nucleus accumbens shape the learning and plasticity of motivated behaviors across species including the regulation of vocal-motor plasticity and performance in songbirds. Discover the latest research on the regulation of vocal-motor plasticity here.

Myocardial Stunning

Myocardial stunning is a mechanical dysfunction that persists after reperfusion of previously ischemic tissue in the absence of irreversible damage including myocardial necrosis. Here is the latest research.