Asymmetric radical addition of ethers to enantiopure N-p-toluenesulfinyl aldimines, mediated by dimethylzinc-air.
Asymmetric radical addition of ethers to enantiopure aromatic N-p-toluenesulfinyl aldimines has been achieved. The requisite radicals were generated by dimethylzinc-air. Lewis acid activation of the N-p-toluenesulfinyl aldimines followed by radical addition gives a mixture of sulfinamide and sulfonamide products. Subsequent treatment of the mixture with dry m-CPBA affords the sulfonamide product in enantiomerically enriched form. [reaction: see text]
Akindele
Tito
T
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Yamamoto
Yasutomo
Y
Maekawa
Masaru
M
Umeki
Hiroyuki
H
Yamada
Ken-ichi
K
Tomioka
Kiyoshi
K
D000388:Air; D002851:Chromatography, High Pressure Liquid; D004987:Ethers / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*; D013449:Sulfonamides; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry*
D004987:Ethers; D005609:Free Radicals; D007097:Imines; D009942:Organometallic Compounds; D013441:Sulfinic Acids; D013449:Sulfonamides; D014050:Toluene; C511262:dimethylzinc