Download PDF by Tsubasa Inokuma: Development of Novel Hydrogen-Bond Donor Catalysts

By Tsubasa Inokuma

ISBN-10: 4431542302

ISBN-13: 9784431542308

ISBN-10: 4431542310

ISBN-13: 9784431542315

This paintings describes novel, potent hydrogen-bond (HB) donor catalysts in keeping with a recognized bifunctional tertiary amine-thiourea, a privileged constitution, which has been confirmed to be the most universal organocatalysts. those HB donor catalysts derived from quinazoline and benzothiadiazine have been at the start synthesized as novel HB donors with their HB-donating skills being measured by means of analytical equipment. They have been chanced on to be potent for various uneven adjustments together with Michael reactions of a, b-unsaturated imides and hydrazination reactions of 1,3-dicarbonyl compounds. Thiourea catalysts that experience an extra practical crew also are defined. particularly, thioureas that undergo a hydroxyl workforce have been synthesized and for this reason used as novel bifunctional organocatalysts for catalytic, uneven Petasis-type reactions concerning organoboronic acids as nucleophiles. those addition reactions have been tough to accomplish utilizing present organocatalysts. one of many constructed catalytic tools will be utilized to the synthesis of biologically attention-grabbing peptide-derived compounds owning unnatural vinyl glycine moieties. those findings introduce new standards required for the advance of organocatalysts for uneven reactions, hence creating a major contribution to the sphere of organocatalysis.

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7; IR (KBr) m 3123, 1678 cm-1; MS (FAB+) 262 (M ? H+, 100); Anal. Calcd. 35. 3; IR (CHCl3) m 3330, 3017, 1739, 1670, 1479 cm-1; MS (FAB+) 220 (M ? H+, 100); HRMS (FAB+) Calcd. 0967. 5; IR (CHCl3) m 3331, 2933, 1699, 1673, 1600, 1479, 1347 cm-1; MS (FAB+) 406 (M ? H+, 54), 135 (100); HRMS (FAB+) Calcd. 2421. 8; IR (CHCl3) m 3314, 2360, 1710, 1683, 1604, 1514, 1478, 1243 cm-1; MS (FAB+) 366 (M ? H+, 92), 135 (100); HRMS (FAB+) Calcd. 00, CHCl3, 92 % ee). 1; IR (CHCl3) m 3316, 3024, 1709, 1683, 1514, 1479, 1217 cm-1; MS (FAB+) 378 (M ?

After concentrated in vacuo, the reaction mixture was purified by silica gel column chromatography with hexane/EtOAc (3/2) to afford desired Michael adduct 12l (127 mg, 94 %). 4; IR (CHCl3) m 3316, 2360, 1753, 1710, 1680, 1476 cm-1; MS (FAB+) 381 (M ? H+, 50), 135 (100); HRMS (FAB+) Calcd. 99, CHCl3). 0036 mmol) at 0 °C. After 4 h, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (hexane/EtOAc = 2/1) to afford desired methylester (17 mg, 92 %).

This result Fig. 2 Asymmetric Michael Addition to a,b-Unsaturated Imides 27 Fig. 13 Kinetic studies on the Michael reaction of malononitrile to imide 11c in the presence of 1a Fig. 14 Michaelis–Menten plot of the Michael addition unambiguously indicates that equilibrium between catalyst 1a and the binary complex of 1a and substrate 11c exists in the 1a-catalyzed Michael addition. Therefore, the reaction constants KM, Vmax and kcat were calculated from the Lineweaver–Burk plot (Fig. 47 M-1 min–1.

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Development of Novel Hydrogen-Bond Donor Catalysts by Tsubasa Inokuma


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