An Efficient Catalytic Sulfonyloxylactonization of Alkenoic Acids Using Hypervalent Iodine(III) Reagent

Abstract

A novel and efficient catalytic method for sulfonyloxylactonization of alkenoic acids is reported. (Diacetoxyiodo)benzene could be used as a recyclable catalyst in combination with m-chloroperbenzoic acid as an oxidant in the presence of sulfonic acid to effect the cyclization of various alkenoic acids in CH₂Cl₂ at room temperature, giving sulfonyloxylactones in good yields.

Key words

sulfonyloxylactonization - hypervalent iodine reagent - catalytic cyclization

References and Notes

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8

Typical Procedure for the Catalytic Sulfonyloxylactonization of Alkenoic Acids
To CH₂Cl₂ (2 mL), alkenoic acid 1 (0.3 mmol),(diacetoxy-iodo)benzene (0.03 mmol), MCPBA (75%, 0.3 mmol) and sulfonic acid 2 (0.3 mmol) were added. The mixture was stirred at r.t. for 24 hours and then H₂O (5 mL), sat. aq Na₂S₂O₃ (2 mL), and sat. aq Na₂CO₃ (2 mL) were added.
The mixture was extracted with CH₂Cl₂ (2 × 5 mL), the combined organic layer was washed with brine, dried over anhyd MgSO₄, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC on a silica gel using (hexane-EtOAc, 2:1) as eluent to give sulfonyloxylacton 3 in good yields.