(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 H-1-NMR, C-13-NMR, COSY, HSQC, IR spectroscopy, HRMS, and the enantiomeric ratio was established by HPLC analysis at the chiral stationary phase.

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate

Arianna Tota
Membro del Collaboration Group
;
Michael Andresini
Membro del Collaboration Group
;
Marco Colella
Membro del Collaboration Group
;
Roberta Savina Dibenedetto
Membro del Collaboration Group
;
Leonardo Degennaro
;
Renzo Luisi
2022-01-01

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 H-1-NMR, C-13-NMR, COSY, HSQC, IR spectroscopy, HRMS, and the enantiomeric ratio was established by HPLC analysis at the chiral stationary phase.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/428503
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