反应详情

温度

-10 °C

Vinylmagnesium bromide (1M in tetrahydrofuran) was cooled under N2 atmosphere to -10° C. and treated in portions with 10 g (37.7 mmol) of N-(t-butyloxycarbonyl)-L-phenylalanine. The resulting solution was stirred at -10° C. for 5 h, and poured into a rapidly stirring mixture of ice, 10% aqueous citric acid and ether. The mixture was separated, and the organic phase was washed sequentially with water, two portions of aqueous NaHCO3, and saturated brine; dried over MgSO4 ; and concentrated in vacuo. Silica gel chromatography of the residue using 4:1 hexane:ethyl acetate provided 3.63 g (35%) of the desired compound (Rf 0.33, 3:1 hexane:ethyl acetate). 1H NMR (CDCl3) δ 1.41 (s, 9 H), 2.98 (dd, J=14, 6 Hz, 1 H), 3.15 (dd, J=14, 6 Hz, 1 H), 4.86 (q, J=8 Hz, 1 H), 5.23 (br d, 1 H), 5.85 (dd, J=9, 2 Hz, 1 H), 6.35 (dd, J=18, 2 Hz, 1 H), 6.45 (dd, J=18, 9 Hz, 1 H), 7.10 (br d, 2 H), 7.25 (m, 3 H). Mass spectrum: (M+H)+ =276.

1. additionpoured into
2. stirringa rapidly stirring
3. customThe mixture was separated
4. washthe organic phase was washed sequentially with water, two portions of aqueous NaHCO3, and saturated brine
5. dry with materialdried over MgSO4
6. concentrationand concentrated in vacuo