[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:12][C:13]([S:16]([NH2:18])=[O:17])([CH3:15])[CH3:14].C([O-])(O)=O.[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[N:18][S:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1An oven dried round-bottom flask was cooled to room temperature by flushing with N2(g) for 30 min. 1,4-Dioxa-spiro[4.5]decan-8-one (1.35 g, 8.66 mmol) (dissolved in 12 mL THF), 2-Methyl-propane-2-sulfinic acid amide (1.0 g, 8.25 mmol) (dissolved in THF), and titanium(IV) ethoxide (3.77 g, 16.50 mmol) were added. The reaction was stirred for 4 h at room temperature. To the mixture was added 15 mL saturated NaHCO3 followed by filtration and an EtOAc rinse. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure yielding 0.98 g of Compound 15.
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