Compound 3h
(1R,1'R)-2,2'-(neopentylazanediyl)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.
Prepared according to the procedure described for compound 3f using neopentylamine (351 µL, 3 mmol) and (R)-styrene oxide (755 µL, 6.6 mmol). After a reaction time of 48 h, purification by column chromatography (hexane/EtOAc 85:15) afforded pure 3h as a yellow oil (599 mg, 61%). 1H NMR (400 MHz, CDCl3) δ7.41–7.26 (m, 10 H, HAr), 4.78 (dd, 2 H, J = 10.2, 3.3 Hz, CHOH), 3.50–3.26 (bs, 2 H, OH), 2.77 (dd, 2 H, J = 13.3, 10.2 Hz, NCHaHbCHOH), 2.70 (dd, 2 H, J = 13.3, 3.3 Hz, NCHaHbCHOH), 2.53 (d, 1 H, J = 14.0 Hz, NCHaHbC(CH3)3), 2.42 (d, 1 H, J = 14.0 Hz, NCHaHbC(CH3)3), 1.04 (s, 9 H, C(CH3)3); 13C NMR (100 MHz, CDCl3) δ142.3 (CqAr), 128.5 (CAr), 127.7 (CAr), 126.0 (CAr), 71.1 (CHOH), 69.0 (NCH2C(CH3)3), 65.5 (NCH2CHOH), 33.0 (C(CH3)3), 28.7 (C(CH3)3); IR νmax (neat/cm-1): 3370, 2950, 1603, 1493, 1481, 1451, 1395, 1361, 1334, 1265, 1202, 1127, 1089, 1061, 1020, 911, 883, 830, 752, 737; HRMS (ESI) calcd for C21H30O2N, [M+H]+: 328.2271, found 328.2279. [α]22D = –90.8 (c = 0.42, CH2Cl2).
- PubChemID:
-
340125612
- MDL Molfile:
- ChemDraw:
