Compound 40
(R)-2-(2-(pyridin-3-yl)ethyl)octanal
From: Direct, enantioselective α-alkylation of aldehydes using simple olefins
View in PubChem | NMR | MDL Molfile | ChemDraw
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Prepared according to the general procedure outlined for compound 13 with 0.02 equiv. Ir[dmppy]2(dtbbpy)PF6(9.7 mg) for 48 hrs. Purified by flash chromatography (30% to 40% EtOAc/hexanes, 1% Et3N) after reduction to the corresponding alcohol to provide the title compound (66 mg, 56% yield, 87% ee) as a colorless oil. Analytical data: [α]D22–1.0 (c = 0.50, CHCl3); 1H NMR (500 MHz, CDCl3) δ 8.49–8.40 (m, 2H), 7.75 (d, J = 7.9 Hz, 1H), 7.41 (dd, J = 7.8, 5.7 Hz, 1H), 3.68–3.62 (m, 1H), 3.60–3.54 (m, 1H), 2.74–2.70 (m, 1H), 2.69–2.65 (m, 1H), 1.79–1.69 (m, 2H), 1.66–1.59 (m, 2H), 1.55 (ddd, J = 15.7, 11.7, 4.3 Hz, 2H), 1.33– 1.24 (m, 7H), 0.88 (t, J = 6.7 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 147.5, 145.1, 140.8, 139.0, 125.1, 65.2, 40.1, 32.5, 31.9, 30.9, 30.4, 29.8, 27.0, 22.8, 14.2; HRMS (ESI+) Calcd. for C15H26NO+H, 235.1936; Found, 235.1929; IR (thin film, cm-1) 3348, 2924, 2855, 1483, 1456, 1442, 1279, 1164, 1131, 1030, 803, 755, 713, 691; HPLC analysis of the alcohol (AD, 10% IPA/Hexanes, 1.0 mL/min) indicates 87% ee: tR= 11.9 (major), 14.6 (minor) min.
