Enantioselective Arylation of 3-Carboxamide Oxindoles with Quinone Monoimines and Synthesis of Chiral Spirooxindole-benzofuranones

Abstract

A highly enantioselective arylation of 3-carboxamide oxoindoles with quinone monoimines is described. Various 3-aryl-3-carboxamide oxindoles with an all-carbon quaternary center were obtained in moderate to good yields (up to 99%) with moderate to good enantioselectivities (up to 98%) in the presence of a bifunctional thiourea-tertiary amine catalyst. The absolute configuration of one product was determined by an X-ray crystal structural analysis and the absolute configurations of the other products can be assigned by analogy. Moreover, several chiral spirooxindole-benzofuranones were synthesized from the 3-aryl-3-carboxamide oxindoles in moderate yields with moderate to good enantioselectivities.

Key words

arylation - 3-carboxamide oxindoles - quinone monoimines - 3,3-disubstitutied oxindoles - spirooxindoles-benzofuranones

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• 14 Enantioselective Arylation of 2-Oxoindoline-3-carboxamide 1 with Quinone Monoimine 2; General Procedure: 2-Oxoindoline-3-carboxamide 1 (0.10 mmol) and catalyst 3i (0.002 mmol, 2 mol%) were dissolved in CHCl₃ (2 mL) in a flame-dried vial equipped with a magnetic stirring bar. After stirring for 30 minutes at –30 °C, quinone monoimine 2 (0.12 mmol, 1.2 equiv) was added. The reaction mixture was stirred at –30 °C until no starting material was detected by TLC. The mixture was subjected to chromatography (silica gel, petroleum ether/EtOAc, 2:1) to afford the desired product 4.
• 15 3-(2-Hydroxy-5-(4-methylphenylsulfonamido)phenyl)-1-methyl-2-oxo-N-phenylindoline-3-carboxamide (4a): Yield: 0.042 g (80%); white solid; mp 169.0–171.5 °C; 95% ee, HPLC condition: Chiralpak Ic-H (n-hexane/ethanol: 70:30, 1.0 mL/min, t _major = 7.476 min, t _minor = 9.122 min); [α]_D ²⁰ = +25.2 (c 1.50, CH₂Cl₂). ¹H NMR (300 MHz, DMSO-d ₆): δ = 9.81 (s, 1 H), 9.67 (s, 1 H), 9.27 (s, 1 H), 7.55 (d, J = 8.0 Hz, 2 H), 7.45 (d, J = 7.9 Hz, 2 H), 7.33 (q, J = 7.5 Hz, 3 H), 7.19 (d, J = 7.9 Hz, 2 H), 7.16–6.98 (m, 4 H), 6.96–6.81 (m, 2 H), 6.58 (d, J = 8.5 Hz, 1 H), 3.22 (s, 3 H), 2.32 (s, 3 H). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 175.33, 164.48, 152.71, 143.96, 143.28, 138.39, 136.97, 129.79, 129.48, 129.16, 128.83, 128.63, 127.14, 126.56, 125.70, 124.54, 123.58, 122.94, 122.76, 120.51, 116.80, 108.88, 63.38, 27.13, 21.44. HRMS (ESI): m/z [M+Na]⁺ calcd. for C₃₀H₂₇N₃O₅SNa⁺: 550.1402; found: 550.1407.