反应详情

To a solution of Methyl (2E)-3-phenylprop-2-en-1-yl carbonate (384 mg) in THF (5 ml), was added N,N-bis[(1S)-1-phenylethyl]dinaphtho[1,2-f:2′,1′-d][1,3,2]dioxaphosphepin-4-amine (108 mg), and chloro(1,5-cyclooctadiene)iridium(I) dimer (27 mg) at RT under N2. The mixture was heated at reflux overnight. Evaporated material then redissoled in a 50:50 mixture of EtOH:THF. To this solution was added macro porous p-toluenesulfonic acid resin (6 g) and the mixture was gently agitated for 3 h. At this time the resin was washed completely with THF, THF:EtOH and EtOH. To a suspension of the resin in MeOH (75 ml) was added 7 N NH3.MeOH (75 ml). This mixture was gently agitated for 2 hours and filered, washing with MeOH, THF, THF:MeOH, and DCM. Evaporating this filtrate left the title compound as a yellow oil (360 mg, 89%). 1H NMR (300 MHz, CDCl3) δ 1.25-1.87 (m, 9H), 2.98-3.07 (m, 1H), 4.24 (d, 1H, J=7 Hz), 5.06-5.21 (m, 2H), 5.87-5.99 (m, 1H), 7.20-7.34 (m, 5H). MS APCI, m/z=202 (M+1), LC/MS, 1.35 min.

1. temperatureThe mixture was heated
2. temperatureat reflux overnight
3. washAt this time the resin was washed completely with THF, THF
4. additionTo a suspension of the resin in MeOH (75 ml)
5. additionwas added 7 N NH3
6. stirringThis mixture was gently agitated for 2 hours
7. washwashing with MeOH, THF, THF
8. customEvaporating this filtrate
9. waitleft the title compound as a yellow oil (360 mg, 89%)
10. customMS APCI, m/z=202 (M+1), LC/MS, 1.35 min.