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First step, koser’s derivative chiral aryl iodine(III) reagents were generated in situ by treating chiral iodobenzene with mCPBA and TsOH . H2O at room temperature using appropriate solvents. Second step involve the addition of small amount of water (22 equiv), followed by addition of alkene 6. The aldehyde formed in this process was reduced in situ adding NaBH4. Iodide 2 and 4 afforded alcohol 7 as non-racemic mixture using CF3CH2OH (TFE)/DCM as mixed solvent (entries 4 and 6, Table 1).

Asymmetric Ring Contraction Reactions Mediated by Chiral I(III)