Compound 2q

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Compound data: HPLC

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

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

1q was attempted to be fluorinated following general procedure A described for compound 3a, using DCM as solvent. 2q was isolated as white solid by flash chromatography (21.9 mg, 39% yield, 13% ee). The ee value was determined by HPLC analysis on a Chiralcel OD-H column (10% isopropanol in hexanes, 0.5 mL/min) with retention time of 25.5 min and 34.9 min. ¹H NMR (600 MHz, CDCl₃): δ 10.48 (s, 1H), 7.60 (d, J = 8.7 Hz, 1H), 7.29 (d, J = 8.8 Hz, 1H), 6.82 (q, J = 6.4 Hz, 1H), 3.91 (s, 3H), 1.69 (d, J = 6.5 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 189.34 (d, J = 5.3 Hz), 157.95, 156.47, 150.38, 147.05 – 146.82 (m), 146.47 – 146.23 (m), 145.31 – 145.09 (m), 145.05 – 144.77 (m), 144.75 – 144.52 (m), 144.21 – 143.96 (m), 143.38 – 143.05 (m), 142.52 – 142.21 (m), 141.81, 138.95 – 138.39 (m), 137.26 – 136.71 (m), 135.06, 126.06, 125.20, 117.65, 108.25 (td, J = 15.9, 3.8 Hz), 106.60 (td, J = 15.1, 4.1 Hz), 71.47, 56.48, 22.55. ¹⁹F NMR (376 MHz, CDCl₃): δ –136.51 (dp, J = 17.8, 6.5 Hz), –138.47 (ddt, J = 16.0, 11.3, 5.1 Hz), –146.48 (tt, J = 20.9, 5.6 Hz), –148.72 (tt, J = 20.8, 4.5 Hz), –159.84 (tq, J = 21.1, 6.9 Hz), –160.46 – –160.66 (m). HRMS (ESI-TOF): m/z calculated for C₂₄H₁₀F₁₀O₆Na⁺ [M+Na]⁺ 607.0210, found 607.0214.