Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine

Abstract

Asymmetric domino reaction of maleimides with γ-halogenated-β-ketoesters catalyzed by quinine is developed to give succinimide substituted 3(2H)-furanones in good enantioselectivities.

Synthesis of Functionalized 5-Amino-3(2H)-furanones via Base-Catalyzed Ring-Cleavage/Recyclization of 4-Cyano-3(2H)-furanones in the Presence of Water

“…1 H NMR (400.1 MHz, CDCl 3 ): δ = 9.23 (br s, 1 H, NH 2 ), 7.89-7.87 (m, 2 H, C 6 H 5 ), 7.36-7.33 (m, 2 H, C 6 H 5 ), 7.16-7.12 (m, 1 H, C 6 H 5 ), 7.07-7.05 (m, 2 H, C 6 H 5 ), 6.99-6.97 (m, 2 H, C 6 H 5 ), 6.11 (br s, 1 H, NH 2 ), 1.47 [s, 6 H, (CH 3 ) 2 ]. 17, 197 (53), 141 (19), 115 (19), 77 (22), 69 (14), 51 13…”

“…IR (KBr): 3355, 2989, 2936, 1618, 1493, 1430, 1372, 1283, 1225, 1200, 1154, 1125, 1060, 476 cm -1 . 6, 135.3, 132.4, 130.2, 129.6, 127.7, 127.3, 126.2, 125.3 14, 128 (26), 127 (67), 69 (19).…”

“…IR (KBr): 3359, 3310, 3097, 3057, 2990, 2943, 1629, 1594, 1491, 1448, 1368, 1346, 1310, 1259, 1238, 1209, 1154, 1129, 1067, 1029 . (11), 201 (14), 177 (17), 176 (38), 160 (30), 159 (100), 136 (37), 135 (17), 133 (11), 132 (14), 131 (10), 120 (45), 108 (19), 104 (16), 94 (49), 93 (31), 92 (29), 80 (14), 78 (10), 69 (28), 68 (19), 67 (19), 66 (29), 65 (59), 58 (12), 51 (10), 43 (12), 41 (36), 40 (11), 39 (45).…”

“…Different synthetic routes have been used for the preparation of 3(2H)-furanones, including an acidor base-catalyzed cyclization/dehydration reaction of 1-hydroxy-2,4-diketones, 7a,13 the hydrogenolysis and subsequent acidic hydrolyses of isoxazoles, 8b the aldol reaction of 3-silyloxyfuranes, 14 condensation of R-acyloxycarbonyl compounds, 3d,15 ionic liquid-catalyzed hydration of diyne alcohols triggered by CO 2 , annulation between α-hydroxy ketones and nitriles, 17 intramolecular cyclization of sulfonium salts, 18 and quinine-catalyzed Michael/O-alkylation reaction of maleimides with γ-halogenated-β-keto esters. 19 In addition, cyclization of acetylenic ketones 20 to 3(2H)-furanones in the presence of Au(III), Ag(I), Cu(I), Hg(II), Pd(II), or Pt(II) has also been described.…”

“…NMR (100.6 MHz, CDCl 3 ): δ = 193.9 (C=O), 191.0 [C(O)Ph], 179.3 (C-5), 138.4, 131.9, 128.8, 127.7 (Ph), 93.7 (C-4), 90.4 (C-2), 23.5 [(CH 3 ) 2 ]. MS (EI): m/z (%) = 231 (45, [M] + ), 230 (67, [M -H] + ), 145 (37), 105 (100), 77 (56), 69 (15), 68(19), 51(19), 41(13).Anal. Calcd for C 13 H 13 NO 3 (231.25): C,67.52; H, 5.67; N, 6.06.…”