京都大学 · 化学
Seijiro Matsubara教授の研究室は、有機合成化学を基盤とし、特に金属触媒を用いた新規反応の開発と、天然物や医薬候材料の効率的合成を主眼としています。Pd/C触媒を用いた水熱的脱カルボキシル化や、ランタニド塩触媒を用いたアミンのコンジュゲート付加反応、およびジメタル化剤や過酸化シリル化剤を用いた酸化・メチレン化反応の開発が特徴です。これらの反応は、反応条件の穏やかさと選択性の高さが特徴で、複雑な天然物の合成に応用可能です。
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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