Reaction Steps
In a procedure similar to that used for the preparation of allylated sulfamide (9b), sulfamide (8e) (250 mg, 0.821 mmol) was subjected standard allylation procedures (K2CO3, allyl bromide, CH3CN 70° C., 24 hours). Flash chromatography (SiO2, Hexanes/EtOAc) yielded 313 mg (99%) of sulfamide (9e) as a clear oil. TLC Rf=0.59 (10:1 Hexanes/EtOAc); [α]25D=+77.5 (c=1.00, CHCl3); 1H NMR (CDCl3, 400 MHz) 7.46 (d, J=7.4 Hz, 4H), 7.39-7.35 (m, 4H), 7.32-7.30 (m, 2H), 5.79 (dddd, J=15.7, 9.7, 7.1, 5.8 Hz, 2H), 5.19 (q, J=7.1 Hz, 2H), 5.03 (dd, J=6.1, 1.3 Hz, 2H), 5.01-4.99 (m, 2H), 3.77 (dd with small allylic coupling, J=16.3, 5.8 Hz, 2H), 3.55 (dd, J=16.3, 7.2 Hz, 2H), 1.67 (d, J=7.1 Hz, 6H); 13C NMR (CDCl3, 100 MHz) 140.1, 135.9, 128.2, 127.9, 127.5, 116.9, 56.5, 47.3, 17.9; FTIR(neat) 3064, 3030, 2980, 2937, 1640, 1603, 1496, 1452, 1378, 1323, 1161, 784, 699 cm−1; HRMS (M+H)+ calculated for C22H29N2O2S 385.1950, found 385.1958.
