Streoselective Synthesis of gamma,delta-Unsaturated beta-Amino Sulfones from Ellman's N-tert-Butylsulfinyl Ketimines and Methyl Phenyl Sulfone

[摘要]：A practical and straightforward approach for the highly stereoselective synthesis of gamma,delta-unsaturated beta-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)-alpha,beta-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)-alpha,beta-unsaturated N-tert-butylsulfinyl ketimines did not exert a significant effect on the outcome of the diastereoselective nucleophilic (phenylsulfonyl) methylation.

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