[O:1]1[CH:9]2[CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8]2.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.O>C(Cl)Cl>[CH2:10]([NH:17][C@@H:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][C@H:9]1[OH:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1To a stirred solution of 5,6-epoxycyclooctene III (10.0 g, 0.081 mol) in dry CH2Cl2 (100 ml) kept under nitrogen atmosphere, benzylamine (10.35 g, 0.097 mol) and Ytterbium(III) trifluoromethanesulfonate (4.96 g, 0.008 mol) were added and the mixture was stirred for 24 hrs at room temperature. Extractive work-up of the reaction mixture with water and CH2Cl2 gave the title product as a white solid (yield 83%). m.p.: 70-71° C., b.p:140° C./1 mm Hg. 1H NMR (CDCl3): δ 7.59-7.56 (m, 2H, ArH), 7.38-7.35 (m, 3H, ArH), 5.64-5.44 (m, 2H, CH=CH), 5.42-5.00 (bs, D2O exchangeable, OH) 4.07 (AB syst, 2H, J=12.57 Hz, PhCH2), 3.75-3.65 (m, 1H, CHOH), 3.00-3.15 (m, 1H, CHNH--), 2.35-2.02 (m, 6H), 1.95-1.42 (m, 2H).
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