(1<i>R</i>,2<i>S</i>,5<i>R</i>)-2-Isopropyl-5-methylcyclohexyl (<i>R</i>)-4-methylbenzenesulfonimidate

Abstract

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate was synthesized via the stereoselective NH-transfer to (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-4-methylbenzenesulfinate. The reaction employed diacetoxyiodobenzene (DIB) and ammonium carbamate, and occurred in acetonitrile at room temperature. The imidation of sulfur proceeded with complete stereocontrol, and the reaction afforded the desired product as a single diastereoisomer and with high enantiocontrol (e.r. = 97:3) in 70% yield. The product was characterized by 1H-NMR, 13C-NMR, COSY, HSQC, IR spectroscopy, HRMS, and the enantiomeric ratio was established by HPLC analysis at the chiral stationary phase.

Keywords

• sulfonimidate
• asymmetric synthesis
• iodonitrene
• sulfur imidation