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Synlett 2012; 23(7): 1031-1034
DOI: 10.1055/s-0031-1290507
DOI: 10.1055/s-0031-1290507
letter
Primary 1,2-Diamine Catalysis (V): Efficient Asymmetric Aldol Reactions of Isatins with Cyclohexanone
Further Information
Publication History
Received: 04 January 2012
Accepted after revision: 06 February 2012
Publication Date:
16 March 2012 (online)
Abstract
1,2-Diaminocyclohexane-hexanedioic acid has been demonstrated to catalyze the asymmetric aldol reactions of cycloketones and various isatin derivatives efficiently in MeOH–H2O. The corresponding products were obtained in good yields (70–90%) with high diastereoselectivity (up to 99:1 anti/syn) and enantioselectivity (up to 99% ee).
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- 13 Typical Procedure To the mixed solvent (2 mL, MeOH–H2O = 1:1) was added the corresponding isatin (0.2 mmol), cyclohexanone (0.6 mmol), and catalyst 13 (0.04 mmol) with equal amount of hexanedioic acid (0.04 mmol). The mixture was stirred at r.t. for 14 h, then quenched with additional H2O. The organic matter was extracted with EtOAc, dried over Na2SO4, and the filtrate was concentrated to get the crude product, which was further purified by a silica gel chromatography. 3-Hydroxy-3-(2-oxocyclohexyl)indolin-2-one (16a) Yield 90%; mp 159 °C; anti/syn = 20:1; 99% ee. 1H NMR (400 MHz, DMSO-d 6): δ = 10.16 (s, 1 H), 7.13–7.21 (m, 2 H), 6.75–6.87 (m, 2 H), 5.77 (s, 1 H), 3.07 (dd, J = 12.0, 4.0 Hz, 1 H), 2.53–2.58 (m, 1 H), 2.36–2.53 (m, 1 H), 2.27–2.34 (m, 1 H), 1.58–2.08 (m, 5 H), 1.43–1.50 (m, 1 H). 13C NMR (100 MHz, DMSO-d 6): δ = 209.8, 179.4, 144.1, 131.5, 129.3, 125.5, 121.5, 110.1, 74.6, 58.1, 42.1, 27.4, 27.3, 25.1. HRMS: m/z calcd for C14H16NO3 [M + H+]: 246.11247; found: 246.11184. The enantiomeric ratio was determined by chiral HPLC with AD-H column (hexane–2-PrOH = 80:20, 1 mL/min)