Compound 5l

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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.

5l was prepared from 3l following general procedure C described for compound 5a (95% ee). The ee value was determined by HPLC analysis on two connected Chiralcel AS-H columns (5% isopropanol in hexanes, 0.5 mL/min) with retention time of 52.5 min (minor) and 57.4 min (major). Absolute stereochemistry was assigned based on the X-ray crystallographic data of compound 5a. ¹H NMR (600 MHz, CDCl₃): δ 7.61 (s, 1H), 7.51 (br s, 4H), 7.38 (dd, J = 8.9, 4.7 Hz, 1H), 7.35 – 7.30 (m, 1H), 5.90 (dq, J = 46.8, 6.3 Hz, 1H), 1.69 (dd, J = 24.1, 6.4 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 160.76, 149.89 (ddd, J = 252.2, 13.4, 2.0 Hz), 147.06 (dd, J = 249.8, 14.2 Hz), 137.40 (dd, J = 20.5, 4.1 Hz), 136.05, 132.23, 124.35 (dd, J = 14.2, 4.9 Hz), 122.31 (ddd, J = 9.2, 6.6, 4.1 Hz), 121.85, 119.14 (d, J = 17.2 Hz), 118.12, 87.94 (dd, J = 167.9, 1.9 Hz), 23.00 (d, J = 25.1 Hz). ¹⁹F NMR (376 MHz, CDCl₃): δ –136.29 (d, J = 22.3 Hz), –139.64 (d, J = 22.1 Hz), –165.75. HRMS (ESI-TOF): m/z calculated for C₁₅H₁₁BrF₃NNaO⁺ [M+Na] ⁺ 379.9868, found 379.9871.