Iodobenzene diacetate → 4-Ethyl-4-methyltetrahydro-1,2,3-oxathiazine 2,2-dioxide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methylpentyl sulfamate from Step 1 (1.25 mmol) in 8 mL of dichloromethane was added sequentially MgO (116 mg, 30 mmol), PhI(OAc)2 (443 mg 1.4 mmol), and Rh2(oct)4 (20 mg, 0.025 mmol). The suspension was stirred vigorously and heated at 40° C. for 3 h. The reaction mixture was cooled to room temperature, diluted with 20 mL of dichloromethane, and filtered through a pad of Celite then concentrated. The crude product was purified by multiple flash chromatographies (5% ethyl acetate/dichloromethane) to give 4-ethyl-4-methyltetrahydro-1,2,3-oxathiazine 2,2-dioxide.

Provenance & Evidence