Stereoselective aza-MIRC reactions on optically active (E)-nitro alkenes

Optically active (E)-nitro alkenes carrying a 1,3-dioxolane or 1,3-oxazolidine residue undergo stereoselective aza-MIRC reactions, leading to the synthesis of the corresponding chiral nitro aziridines in high yields and with good diastereoselectivity. Interestingly, the stereochemical outcome of the aziridination reactions was strongly influenced by the chiral residue considered, giving stereoisomers, regardless of the reaction conditions.

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tert-Butyl (4S)-4-[(2′S,3′S)-1′-(ethoxycarbonyl)-3′-nitroaziridin-2′-yl]-2,2-dimethyloxazolidine-3-carboxylateC15H25N3O7De > 99%[α]D = +2.2 (c 1.0, CHCl3)Source of chirality: chemical reactionAbsolute configuration: (4S,2′S,3′S)

tert-Butyl (4S)-4-[(2′S,3′R)-1′-(ethoxycarbonyl)-3′-nitroaziridin-2′-yl]-2,2-dimethyloxazolidine-3-carboxylateC15H25N3O7De > 99%[α]D = +1.9 (c 1.0, CHCl3)Source of chirality: chemical reactionAbsolute configuration: (4S,2′S,3′R)

tert-Butyl (4S)-4-[(2′S,3′S)-1′-(ethoxycarbonyl)-3′-methyl-3′-nitroaziridin-2′-yl]-2,2-dimethyloxazolidine-3-carboxylateC16H27N3O7De > 99%[α]D = +1.9 (c 1.0, CHCl3)Source of chirality: chemical reactionAbsolute configuration: (4S,2′S,3′S)

tert-Butyl (4S)-4-[(2′S,3′R)-1′-(ethoxycarbonyl)-3′-methyl-3′-nitroaziridin-2′-yl]-2,2-dimethyloxazolidine-3-carboxylateC16H27N3O7De > 99%[α]D = +2.15 (c 1.0, CHCl3)Source of chirality: chemical reactionAbsolute configuration: (4S,2′S,3′R)

tert-Butyl (4S)-4-{(2′S,3′S)-1′-[(phenylmethoxy)carbonyl]-3′-nitroaziridin-2′-yl}-2,2-dimethyloxazolidine-3-carboxylateC20H27N3O7De > 99%[α]D = +2.7 (c 1.0, CHCl3)Source of chirality: chemical reactionAbsolute configuration: (4S,2′S,3′S)

tert-Butyl (4S)-4-{(2′S,3′R)-1′-[(phenylmethoxy)carbonyl]-3′-nitroaziridin-2′-yl}-2,2-dimethyloxazolidine-3-carboxylateC20H27N3O7De > 99%[α]D = +2.0 (c 1.0, CHCl3)Source of chirality: chemical reactionAbsolute configuration: (4S,2′S,3′R)