Compound 6b

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InChIKey OTKJACSRALAJRD-BVRKHOPBSA-N

Compound data: CIF

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

Compound 6b was synthesized by the general method outlined for compound 6a. White solid; mp: 85-90^oC; 93% yield; ¹H NMR (400MHz, CDCl₃): δ 7.25-7.23 (m, 3 H), 7.18-7.13 (m, 5 H), 7.08 (dd, J₁ = 6.7 Hz, J₂ = 7.9 Hz, 1 H), 6.93-6.97 (m, 3 H), 6.78 (dd, J₁ = 6.8 Hz, J₂ = 8.3 Hz, 1 H), 6.67 (d, J = 8.4 Hz, 2 H), 6.51 (t, J = 7.3 Hz, 1 H), 6.45 (d, J = 8.2 Hz, 1H), 6.30 (d, J = 7.3 Hz, 2 H), 5.69 (d, J = 8.9 Hz, 1 H), 4.98 (d, J = 8.5 Hz, 1 H), 3.68 (s, 3 H), 3.55 (s, 3 H); ¹³C NMR (100Hz, CDCl₃): δ 172.97, 145.85, 140.70, 138.64, 136.40, 132.46, 131.00, 130.45, 129.14, 128.88, 128.15, 127.81, 127.20, 121.38, 119.46, 117.29, 113.03, 109.49, 61.74, 60.80, 52.20, 32.94; IR (neat): U 2954, 2929, 2856, 1963, 1717, 1602, 1507, 1469, 1252, 1156, 1089, 1066, 835, 777, 743, 698 cm^-1; dr (anti:syn) > 20:1; HRMS (ESI) Calcd for [C₃₁H₂₇BrN₂NaO₂, M + Na]⁺ : 561.1148; found: 561.1138; 99% ee (HPLC condition: Chiralcel IA column, n-Hexane/i-PrOH = 90:10, flow rate = 1.0 mL/min, wave length = 254nm, t_R = 7.40 min for major isomer, t_R = 8.59 min for minor isomer); [α]_D¹⁰ +4.3 (c 0.68, CH₂Cl₂).