C(N(CC)CC)C.[CH2:8]([C:11]1([CH2:18][CH:19]=[CH2:20])[CH2:15][NH:14][C@@H:13]([CH2:16][OH:17])[CH2:12]1)[CH:9]=[CH2:10].[S:21](Cl)(Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH2:18]([C:11]1([CH2:8][CH:9]=[CH2:10])[CH2:15][N:14]2[S:21](=[O:23])(=[O:22])[O:17][CH2:16][C@H:13]2[CH2:12]1)[CH:19]=[CH2:20]A solution of triethylamine (2.460 ml, 17.65 mmol) and (R)-(4,4-diallylpyrrolidin-2-yl)methanol (1.60 g, 8.83 mmol) in DCM (44.1 ml) was cooled to −78° C. To this mixture was added sulfuryl chloride (0.859 ml, 10.59 mmol) in DCM (44 mL) dropwise in 1 h. The reaction was maintained at this temperature for 3 h, then allowed to warm to room temperature and stirred overnight. The mixture washed with aq. 1 N HCl (30 ml×2), brine (30 ml), dried, filtered and concentrated. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a REDISEP™ pre-packed silica gel column (40 g), eluting with a gradient of 0% to 30% EtOAc in hexane, to provide (R)-5,5-diallyltetrahydro-3H-pyrrolo[1,2-c][1,2,3]oxathiazole 1,1-dioxide (0.66 g, 2.71 mmol, 30.7% yield) as light-yellow oil. 1H NMR (400 MHz, CDCl3) δ 5.71-5.86 (m, 2H), 5.10-5.20 (m, 4H), 4.57 (dd, J=6.63, 8.76 Hz, 1H), 4.24-4.36 (m, 1H), 4.19 (dd, J=4.66, 8.76 Hz, 1H), 3.21-3.32 (m, 2H), 2.19-2.29 (m, 4H), 2.03-2.18 (m, 1H), 1.57-1.63 (m, 1H).
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