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Kimura Lab
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A lab that develops organic synthetic reactions by making use of the reactivity of magnesium carbenoids.
AboutAbout the lab
Developing new synthetic reactions by making use of unique reactivity
The Kimura Lab is an organic chemistry lab that works on developing reactions that make use of the unique reactivity of magnesium carbenoids.
Organic compounds are used in daily life as pharmaceuticals, agrochemicals, fragrances, dyes, and chemical products, and organic reactions are essential for making them.
The lab aims to develop reactions that can synthesize organic compounds efficiently and with high selectivity.
The lab investigates the mechanisms of reactions using computational chemistry.
Key terms
- Magnesium carbenoid
- A species in which magnesium and a leaving group (usually a halogen) are bonded to a single carbon. It shows reactivity similar to that of carbenes.
- Sulfoxide
- An organic compound in which oxygen is bonded to sulfur. The sulfur is chiral, so it can be used in asymmetric synthesis.
- Asymmetric synthesis
- Synthesis that selectively produces more of one of two molecules that are mirror images of each other.
ResearchResearch themes
Aiming to develop reactions that can synthesize organic compounds efficiently and with high selectivity, the lab conducts research that makes use of the unique reactivity of magnesium carbenoids. The lab investigates the mechanisms of reactions using computational chemistry.
*Illustrative imageNucleophilic reactions of magnesium carbenoids
Like Grignard reagents, magnesium carbenoids act as nucleophiles. When they are generated from α-chloro-substituted sulfoxides that have an electrophilic functional group, the reaction takes place intramolecularly and forms cyclic compounds.
*Illustrative imageElectrophilic reactions of magnesium carbenoids
Although magnesium carbenoids are organometallic species, they react with nucleophiles. When the resulting organomagnesium intermediate is reacted with an electrophile, the carbenoid, the nucleophile, and the electrophile, three components in total, can be joined in one pot.
*Illustrative imageRearrangement reactions of magnesium carbenoids
Magnesium carbenoids insert into C–H and C–C bonds following α-elimination of magnesium chloride. By making good use of this high reactivity, bonds that are usually considered inert can be modified.
*Illustrative imageAsymmetric synthesis using the sulfinyl group
When α-chloro-substituted sulfoxides synthesized from optically active chloromethyl p-tolyl sulfoxide or dichloromethyl p-tolyl sulfoxide are used as carbenoid precursors, various compounds can be synthesized with high enantiomeric excess.
MembersFaculty
The members of the Kimura Lab consist of faculty members, doctoral students, master's students, and undergraduate students.
- Associate ProfessorTsutomu Kimura
VoicesStudent voices
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Report an errorAbout the images
The top and research theme images are illustrative and were not taken at the lab. They are cropped from Wikimedia Commons images. Cropped CC BY-SA images are provided under the same CC BY-SA license as the original (version shown on each line).
- Top image: “Grignard reaction experiment 01” Calvero / CC BY-SA 3.0 (cropped)
- Nucleophilic reactions of magnesium carbenoids: “Organic lab Department of Chemistry DU” Mir Mahadi Hassan / CC BY-SA 3.0 (cropped)
- Electrophilic reactions of magnesium carbenoids: “ThermiteReaction” User:Nikthestunned (Wikipedia) / CC BY-SA 3.0 (cropped)
- Rearrangement reactions of magnesium carbenoids: “Organic Chemistry Lab 5 by marthou” Marthou / CC BY-SA 4.0 (cropped)
- Asymmetric synthesis using the sulfinyl group: “Soviet portable polarimeter in its case” Siarhei Besarab / CC BY-SA 4.0 (cropped)
- Related lab (佐竹研究室): “Host Guest Complex Porphyrin Sanders AngewChemIntEdEngl” M stone at English Wikipedia / CC BY-SA 3.0 (cropped)
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