Kyoto University · Chemistry
Professor Seijiro Matsubara's research lab specializes in organic synthesis and catalysis, with a focus on developing novel metal-catalyzed and Lewis acid-mediated transformations for the efficient construction of complex organic molecules. Key research directions include decarboxylative and decarbonylative functionalization of carboxylic acids and aldehydes under mild or hydrothermal conditions, stereoselective conjugate additions to unsaturated systems, and innovative methods for C–C and C–heteroatom bond formation using organometallic reagents and peroxides. The lab also explores the use of tailored metal complexes and non-traditional reagents for selective oxidation and methylenation reactions.
Figures are computed from collected data and may differ slightly.
[reaction: see text] Decarboxylation of free carboxylic acid was performed by Pd/C catalyst under hydrothermal water (250 degrees C/4 MPa). Under the hydrothermal conditions of deuterium oxide, decarbonylative deuteration was observed to give fully deuterated hydrocarbons from carboxylic acids or aldehydes.
Abstract Catalytic amount of lanthanoid(III) triflates promoted the conjugate addition of amines to 2-alkenoic acid esters to give β-amino esters. The reaction of benzylamine with α,β-unsaturated esters containing a stereogenic center at γ-position proceeded diastereoselectivity to yield optically active β-lactam precursors.
Nysted reagent [cyclo-dibromodi-µ-methylene(µ-tetrahydrofuran)trizinc], a commercially available gem-dimetallic compound, reacted with aldehydes affording methylenated products in the presence of BF3·OEt2, whereas methylenation of ketones proceeded in the presence of BF3·OEt2 and TiCl2.
Abstract Treatment of ketones with bis(trimethylsilyl) peroxide and Lewis acid such as SnCl4 or BF3·OEt2 in dichloromcthane at room temperature affords esters in fair to excellent yields. Jasmine lactone is synthesized from 2-[(Z)-2-pentenyl]cyclopentanone by means of Me3SiOOSiMe3–BF3·OEt2 system without any protection of the carbon-carbon double bond. The oxidation of enol acetates of ketones to α-hydroxy (or α-acetoxy) ketones with Me3SiOOSiMe3–FeCl3 system is also disclosed.
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