Compound 3f
(1R,1'R)-2,2'-(benzylazanediyl)bis(1-phenylethan-1-ol)
From: Enantioselective cyclizations and cyclization cascades of samarium ketyl radicals
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a solution of (R)-styrene oxide (1.26 mL, 11 mmol) in MeOH (10 mL) was added benzylamine (547 µL, 5 mmol). The reaction mixture was refluxed for 36 h, after which completion was observed by TLC. Volatiles were removed in vacuo, and the crude mixture was purified by column chromatography (hexane/EtOAc 80:20), affording the product as a colorless oil turning to an amorphous white solid upon drying (average: 1.13 g, 3.25 mmol, 65%). 15% of isomeric diol was also isolated. 1H NMR (400 MHz, CDCl3) δ7.39–7.24 (m, 15 H, HAr), 4.76 (dd, 2 H, J = 9.6, 3.8 Hz, CHOH), 4.00 (d, 1 H, J = 13.5 Hz, NCHaHbPh), 3.69 (d, 1 H, J = 13.5 Hz, NCHaHbPh), 3.23 (bs, 2 H, OH), 2.82 (dd, 2 H, J = 13.5, 9.6 Hz, NCHaHbCHOH), 2.76 (dd, 2 H, J = 13.5, 3.8 Hz, NCHaHbCHOH); 13C NMR (100 MHz, CDCl3) δ142.1 (CqAr), 138.0 (CqAr), 129.2 (CAr), 128.7 (CAr), 128.5 (CAr), 127.7 (CAr), 127.6 (CAr), 125.9 (CAr), 70.9 (CHOH), 62.7 (NCH2CHOH), 59.9 (NCH2Ph); HRMS (ESI) calcd for C23H26O2N, [M+H]+: 348.1964, found 348.1971, consistent with literature data.
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340125610
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