3,3-Dimethyl-1-butyne → HCID 68917890, compound

Participants

Reaction Steps

The product was prepared by General procedure S using 98 mg (0.55 mmol) Cy2BH, 68 μL (0.55 mmol) 3,3-dimethyl-1-butyne, 0.55 mL (1.1 mmol, 2.0 M in hexanes) Et2Zn, 4.8 mg (0.02 mmol) (−)-MIB, and 61 μL (0.50 mmol) cyclohexane-carboxaldehyde. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 80% yield (78 mg, 0.40 mmol). [α]D20=−27.7 (c=0.13, CHCl3, 96% ee); 1H NMR (CDCl3, 500 MHz): δ 0.92-0.97 (m, 2H), 1.01 (s, 9H), 1.11-1.26 (m, 4H), 1.41 (m, 1H), 1.64 (m, 2H), 1.73 (m, 2H), 1.86 (br d, 1H, J=12.6 Hz), 3.75 (t, 1H, J=7.0 Hz), 5.35 (dd, 1H, J=15.6, 7.5 Hz), and 5.62 (d, 1H, J=15.7 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz): δ 26.1, 26.2, 26.6, 28.76, 28.84, 29.6, 32.9, 43.8, 77.9, 126.2, and 143.9 ppm; IR (neat): 3351, 2953, 2926, 2853, 1655, 1473, 1450, 1387, 1362, 1305, 1260, and 1204 cm−1; HRMS-CI m/z 195.1743 [(M−H)+; calcd for C13H23O: 195.1749].

Provenance & Evidence