The University of Osaka · Chemistry
Professor Masaru Kondo's research lab specializes in the development of asymmetric catalysis, with a focus on enantioselective transformations of nitrile and imine derivatives. The lab pioneers novel catalytic systems—particularly chiral Pd(II) and bis(imidazoline) catalysts—for the efficient synthesis of enantiopure β-aminonitriles, α,α-diaminonitriles, and functionalized vinylidene-aminonitriles. Recent work also explores stimuli-responsive chiral catalysts, such as azo-crown ether-based photoswitchable phase-transfer catalysts, enabling light-controlled reactivity and selectivity. The lab's research bridges fundamental catalysis with applications in pharmaceutical synthesis and sustainable methodology development.
Figures are computed from collected data and may differ slightly.
In this study, FLT3/ITD was observed in 11% of childhood AML and identified to be associated with poor prognosis. A large prospective study with uniform treatment is necessary to confirm our results.
The catalytic enantioselective reaction of diphenylmethylidene-protected α-aminoacetonitriles with imines has been developed. Good yields and diastereo- and enantioselectivities were observed for the reaction of various imines using chiral bis(imidazoline)/Pd catalysts. The reaction of α-aminonitriles with di-tert-butyl azodicarboxylate afforded chiral α,α-diaminonitriles in high yields with high enantioselectivities.
The catalytic enantioselective reaction of α-phenylthioacetonitriles with imines has been developed. The reaction of various imines proceeds in good yields and diastereo- and enantioselectivities in the presence of chiral bis(imidazoline)-palladium catalysts. The obtained products can be converted into β-aminonitrile or β-aminoamide compounds without loss of enantiopurity.
The first highly enantioselective reaction of allenylnitriles with imines has been developed. Excellent yields and enantioselectivities were observed for the reaction with various imines using chiral Phebim-Pd<sup>II</sup> complexes. This process offers a simple and efficient synthetic route for various functionalized α-vinylidene-β-aminonitriles and their derivatives.
Azo-crown ether-based photoswitching chiral phase transfer catalysts have been developed to control the catalytic activity by photoirradiation. Azobenzene binaphthyl crown ether (ABCE) can switch its reactivity and selectivity through structural transformation of the crown ether moiety induced by E/Z photoisomerization of azobenzene. (Z)-ABCE promoted enantioselective alkylation of the glycine Schiff base to afford chiral amino acid derivatives in good yields with high enantiomer ratios. In cont
The catalytic enantioselective Mannich-type reaction of dichloroacetonitrile with imines has been developed. Good yields and enantioselectivity were observed for the reaction with various imines using chiral bis(imidazoline) catalysts. β-Aminonitriles or β-aminoamide were obtained from products without the loss of enantiopurity.
Traditional optimization methods using one variable at a time approach waste time and chemicals and assume that different parameters are independent from one another. Hence, a simpler, more practical, and rapid process for predicting reaction conditions that can be applied to several manufacturing environmentally sustainable processes is highly desirable. In this study, biaryl compounds were synthesized efficiently using an organic Brønsted acid catalyst in a flow system. Bayesian optimization-a
The Mills reaction and cyclization of readily available 2-aminobenzyl alcohols and nitrosobenzenes using thionyl bromide provided 2H-indazoles in up to 88 % yields. In the metal-free process, acetic acid played a crucial role for the both Mills reaction and cyclization. A brominated 2H-indazole could also be obtained through the one-pot sequence.
An azopyridine-based oxazoline was developed for utilizing azo group coordination and isomerization as a photoswitchable ligand. The ligand coordinated to rare-earth metal (RE) catalyst underwent efficient E/Z photoisomerization, suggesting tri- and bidentate coordination switching. The photoisomerization of the ligand enabled modulation of the enantioselectivity of an RE-catalyzed aminal forming reaction.
The first highly enantioselective reaction of α,α-dithioacetonitriles with imines has been developed. Good yields and enantioselectivity were observed for the reaction of various imines using chiral bis(imidazoline) catalysts. The obtained products can be converted into β-aminonitrile or 1,3-diaminoketone.
We examined the Chan–Lam cross-coupling of imidazole and arylboronic acids under additive-free and mild conditions using heterogeneous CuO/MO X catalysts such as metal oxide-supported CuO and Cu-doped metal oxides.
Correction for ‘Exploration of flow reaction conditions using machine-learning for enantioselective organocatalyzed Rauhut–Currier and [3+2] annulation sequence’ by Masaru Kondo <italic>et al.</italic>, <italic>Chem. Commun.</italic>, 2020, <bold>56</bold>, 1259–1262, DOI: 10.1039/C9CC08526B.
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