By Tsubasa Inokuma
This paintings describes novel, potent hydrogen-bond (HB) donor catalysts in response to a recognized bifunctional tertiary amine-thiourea, a privileged constitution, which has been confirmed to be essentially the most conventional organocatalysts. those HB donor catalysts derived from quinazoline and benzothiadiazine have been at the start synthesized as novel HB donors with their HB-donating talents being measured via analytical tools. They have been chanced on to be powerful for a number of uneven differences together with Michael reactions of a, b-unsaturated imides and hydrazination reactions of 1,3-dicarbonyl compounds. Thiourea catalysts that experience an extra useful crew also are defined. particularly, thioureas that undergo a hydroxyl crew have been synthesized and consequently used as novel bifunctional organocatalysts for catalytic, uneven Petasis-type reactions regarding organoboronic acids as nucleophiles. those addition reactions have been tricky to accomplish utilizing latest organocatalysts. one of many constructed catalytic equipment should 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 improvement of organocatalysts for uneven reactions, hence creating a major contribution to the sector of organocatalysis.
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00, CHCl3). 207 mmol) and the solution was stirred at room temperature for 4 h. 5 mg, 90 %). 6; IR (CHCl3) m 3021, 1711, 1436, 1419 cm-1; MS (FAB+) 318 (M ? H+, 40), 105 (100); HRMS (FAB+) Calcd. 1707. 21, CHCl3, 92 % ee). 86 mL) was stirred at 60 °C for 168 h. After concentrated in vacuo, the reaction mixture was purified by silica gel column chromatography with hexane/EtOAc (3/1) to afford desired Michael adduct 12p (102 mg, 56 %). 4; IR (CHCl3) m 3320, 3024, 1710, 1684, 1555, 1479, 1379 cm-1; Anal.
4; IR (CHCl3) m 3025, 2251, 1734 cm-1; MS (CI+) 142 (M ? 28, CHCl3, 92 % ee). 5; IR (CHCl3) m 3323, 2933, 1753, 1709, 1684, 1479 cm-1; MS (FAB+) 505 (M ? H+, 28); HRMS (FAB+) Calcd. 67, CHCl3). 0; IR (CHCl3) m 3021, 1747, 1711, 1362 cm-1; MS (FAB+) 272 (M ? H+, 100); HRMS (FAB+) Calcd. 00, CHCl3). 5; IR (CHCl3) m 3021, 2360, 1732, 1439 cm-1; MS (FAB+) 214 (M ? H+, 98), 154 (100); HRMS (FAB+) Calcd. 00, CHCl3). 207 mmol) and the solution was stirred at room temperature for 4 h. 5 mg, 90 %). 6; IR (CHCl3) m 3021, 1711, 1436, 1419 cm-1; MS (FAB+) 318 (M ?
2, CH3CN) in 96 % yield. 1, CH3CN). 20, CHCl3). Based on a comparison of the specific rotations of 13, 14 and 15 with the literature, the absolute configurations of 13, 14 and 15 were determined to be R, S and S, respectively. 3). Almost all of the 1H NMR signals such as the vinylic protons (Ha and Hb) of 11a, c, d and e possessed similar chemical shifts; the signal of the N–H proton of 11c was observed downfield as compared to those of 11a and d, e. 01 M, CHCl3) appeared at a slightly lower wavenumber (3330 cm-1) than those of 11a and d, and e (3391–3405 cm-1).