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A novel "umpolung" intramolecular cyclization of alkynyl imines, in which the electrophilic imine sp2‐carbon formally serves as a nucleophilic site, was developed under Brønsted base catalysis. The reaction involves the unprecedented catalytic generation of α‐aminoester enolates from α‐iminoesters via the 1,2‐addition of the anion of a secondary phosphite to an imine moiety followed by the [1,2]‐rearrangement of a dialkoxyphosphoryl moiety from carbon to nitrogen, which is a formal umpolung process, and the intramolecular addition to an alkyne. This is a rare example of a [1,2]‐rearrangement of a dialkoxyphosphoryl moiety from carbon to nitrogen to generate an α‐amino carbanion and the first catalytic carbon‐carbon bond forming reaction utilizing the resulting carbanion as a nucleophile.
| Authors: | Azusa Kondoh, Masahiro Terada | |
| Journal: | Chemistry - A European Journal | |
| Year: | 2018 | |
| Pages: | n/a | |
| DOI: | 10.1002/chem.201800219 | |
| Publication date: | 17-Jan-2018 |
The unfolding landscape of the congenital myasthenic syndromes
Abstract Congenital myasthenic syndromes (CMS) are heterogeneous disorders in which the safety margin of neuromuscular transmission is impaired by one or more specific mechanisms. Since the advent of next‐generation sequencing methods, the discovery of novel CMS targets and phenotypes ha ... more
Passive transfer models of myasthenia gravis with muscle‐specific kinase antibodies
Abstract Myasthenia gravis (MG) with antibodies to muscle‐specific kinase (MuSK) is characterized by fluctuating fatigable weakness. In MuSK MG, involvement of bulbar muscles, neck, and shoulder and respiratory weakness are more prominent than in acetylcholine receptor (AChR) MG. MuSK au ... more
Abstract Because of the failure of many promising therapeutics identified in preclinical evaluation, funding sources have established guidelines for increased rigor in animal evaluations. The myasthenia gravis (MG) community of scientists has developed guidelines for preclinical assessme ... more
Smart skin made of recyclable materials may transform medicine and robotics
Smart skin that can respond to external stimuli could have important applications in medicine and robotics. Using only items found in a typical household, researchers have created multi-sensor artificial skin that's capable of sensing pressure, temperature, humidity, proximity, pH, and air ... more
How mercury contamination affects reptiles in the Amazon basin
Mercury contamination in water and on land is of worldwide concern due to its toxic effects on ecosystems and human health. Mercury toxicity is of particular concern to reptiles because they are currently experiencing population declines. Also, reptiles are ideal indicators of mercury conta ... more
Bioengineers Succeed in Producing Plastic Without the use of Fossil Fuels
A team of pioneering South Korean scientists have succeeded in producing the polymers used for everyday plastics through bioengineering, rather than through the use of fossil fuel based chemicals. This groundbreaking research, which may now allow for the production of environmentally consci ... more
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