Abstract
A practical and straightforward approach for the highly stereoselective synthesis of γ,δ-unsaturated β-amino sulfones by nucleophilic (phenylsulfonyl)methylation of N-tert-butylsulfinyl ketimines with methyl phenyl sulfone was achieved. With lithium bis(trimethylsilyl)amide as the base, the corresponding sulfone-stabilized carbanion derived from methyl phenyl sulfone can be transferred to (S)-α,β-unsaturated N-tert-butylsulfinyl ketimines in very good yields and with high diastereoselectivities. Electron-withdrawing or electron-donating substituents on the aryl rings of (S)-α,β-unsaturated N-tert-butylsulfinyl ketimines did not exert a significant effect on the outcome of the diastereoselective nucleophilic (phenylsulfonyl) methylation.
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