Compound 5ba

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InChIKey OHVICNNAOFIKGB-LADGPHEKSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

A mixture of Rh₂(OAc)₄ (0.002 mmol), imine 2a (0.1 mmol), 7b (0.01 mmol) in 1.0 mL CH₂Cl₂ under an argon atmosphere was stirred at the -20°C. Diazo compound 1b (0.2 mmol) in 1.0 mL CH₂Cl₂ was added over 1hr via a syringe pump. After the completion of the addition, the reaction was stirred at -20°C for another 1hr and evaporated under reduced pressure to give the crude product. The crude product was purified by flash chromatography on silica gel (eluent: EtOAc/light petroleum ether = 1:15 ~ 1:5) to give the pure product. White solid; mp: 119-125^oC; 77% yield; ¹H NMR (500MHz, CDCl₃): δ 7.28-7.26 (m, 3 H), 7.19 (t, J = 6.9 Hz, 1 H), 7.09 (t, J = 7.3 Hz, 1 H), 7.01-6.96 (m, 6 H), 6.96-6.54 (m, 3 H), 6.15 (d, J = 8.6 Hz, 1 H), 4.76 (d, J = 8.8 Hz, 1 H), 2.99 (s, 3 H), 2.49-2.45 (m, 1 H), 2.00-1.95 (m, 1 H), 0.63 (t, J = 7.4 Hz, 3 H); ¹³C NMR (100MHz, CDCl₃): δ 178.67, 145.74, 144.00, 138.04, 131.71, 129.34, 128.27, 127.69, 127.33, 127.23, 123.84, 123.35, 114.84, 108.61, 107.92, 62.65, 57.38, 27.94, 25.79, 8.77; IR (neat): U 3393, 2963, 2923, 2853, 1698, 1601, 1498, 1468, 1401, 1353, 1318, 1259, 1089, 1076, 1020, 824, 804, 753, 726, 704 cm^-1; dr (syn:anti) = 98:2; HRMS (ESI) Calcd for [C₂₄H₂₃ClN₂NaO, M + Na]⁺: 413.1397; found: 413.1377; 96% ee (HPLC condition: Chiralcel IA column, n-Hexane/i-PrOH = 95:5, flow rate = 1.0 mL/min, wave length = 254nm, t_R = 9.97 min for minor isomer, t_R = 12.58 min for major isomer); [α]_D¹⁰ +68.9 (c 1.14, CH₂Cl₂).