Compound 7o
(R)-2,4-Dimethylpentan-3-yl 3-(2-benzoyl-1-benzylhydrazinyl)-3-(3-chlorophenyl)-2-diazopropanoate
From: Generation and exploitation of acyclic azomethine imines in chiral Brønsted acid catalysis
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InChIKey URBZDWJGUHPBPE-HHHXNRCGSA-N
Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Prepared according to the general procedure for 7a with 3-chlorobenzaldehyde (0.15 mmol, 21.0 mg) and 2,4-dimethyl-3-pentyl 2-diazoacetate 6 (0.12 mmol, 22.1 mg) at 0 °C. The crude material was purified by column chromatography on silica gel (eluting with hexane/EtOAc = 5:1) to give 7o as a yellow solid [57% (30.3 mg)]. Enantiomeric purity was determined by HPLC analysis (Daicel Chiralcel OD-H, hexane/2-propanol = 100:1, flow rate = 0.3 mL/min, retention time; 36.9 min (major), 41.7 min (minor)). 1H NMR (400 MHz, CDCl3, 50 °C) δ 7.55-7.50 (2H, m), 7.45-7.35 (5H, m), 7.33-7.23 (8H, m), 5.29 (1H, s), 4.58 (1H, t, J = 6.4 Hz), 4.23 (1H, d, J = 13 Hz), 4.15 (1H, d, J = 13 Hz), 1.93-1.77 (2H, m), 0.88-0.79 (6H, m), 0.75-0.67 (6H, m); 13C NMR (100 MHz, CDCl3, 50 °C) δ 166.8, 166.7, 140.4, 136.3, 134.9, 133.6, 131.4, 130.3, 129.3, 128.6, 128.5, 128.4, 127.8, 127.5, 126.9, 125.7, 84.2, 63.6, 58.0, 29.6, 29.5, 19.6, 19.4, 17.2, 17.1 cm-1; IR (neat) 3259, 2967, 2095, 1688, 1470, 1369, 1288, 1248, 1094 cm-1; HRMS (ESI) exact mass calcd for C30H33ClN4O3: m/z 555.2133 ([M + Na]+), found: m/z 555.2123 ([M + Na]+). [α]26D = +56.2 (c = 1.0, CHCl3, 90% ee).
