The title compound, 5-methoxy-butyrolacto[3,4-b]-1-N-cyclohexylaziridine 1, has been synthesized via tandem Micheal addition and intramolecular nucleophilic substitution reactions of 5-methoxy-3-bromo-2(5H)-furanone...The title compound, 5-methoxy-butyrolacto[3,4-b]-1-N-cyclohexylaziridine 1, has been synthesized via tandem Micheal addition and intramolecular nucleophilic substitution reactions of 5-methoxy-3-bromo-2(5H)-furanones 4 with primary amines 5, and structurally determined by single-crystal X-ray diffraction. Crystal data: C11H17NO3, Mr = 211.26, monoclinic system, space group P21/c, a = 17.800(3), b = 5.3864(10), c = 12.2571(10)A°, β = 90.449(3)°, V = 1175.1(3) A°^3, Z= 4, De= 1.194 g/cm^3, λ(MoKα) = 0.071073 nm, μ = 0.087 mm^-1 and F(000) = 456. The structure was refined to R = 0.0505 and wR = 0.1208 for 2579 observed reflections (I 〉 2σ(I)). The crystallographic results of molecule 1 show that the functionalized aziridine ring is fused with a lactone ring to form the component with [3.1.0] bicyclic skeleton.展开更多
Chiral butyrolacto[3,4-b]-2(S)-6(R)-1-N-akylaziridines 7 were synthesized in enantiopure form utilizing racemic 5-methoxy-3-bromo-2(5H)-furanone (5) and available amines (6) as key precursors. After highly effective r...Chiral butyrolacto[3,4-b]-2(S)-6(R)-1-N-akylaziridines 7 were synthesized in enantiopure form utilizing racemic 5-methoxy-3-bromo-2(5H)-furanone (5) and available amines (6) as key precursors. After highly effective reduction of 7, the functionalized 2(S),3(R)-dihyroxymethyl-N-alkylaziridines (8) were obtained in good yields with ≥98% ee. This is a simple and pratical method for the preparation of enantiopure aziridines which are important interme-diates in the synthesis of biologic active molecules.展开更多
基金Supported by the National Natural Science Foundation of China (No. 29672004)
文摘The title compound, 5-methoxy-butyrolacto[3,4-b]-1-N-cyclohexylaziridine 1, has been synthesized via tandem Micheal addition and intramolecular nucleophilic substitution reactions of 5-methoxy-3-bromo-2(5H)-furanones 4 with primary amines 5, and structurally determined by single-crystal X-ray diffraction. Crystal data: C11H17NO3, Mr = 211.26, monoclinic system, space group P21/c, a = 17.800(3), b = 5.3864(10), c = 12.2571(10)A°, β = 90.449(3)°, V = 1175.1(3) A°^3, Z= 4, De= 1.194 g/cm^3, λ(MoKα) = 0.071073 nm, μ = 0.087 mm^-1 and F(000) = 456. The structure was refined to R = 0.0505 and wR = 0.1208 for 2579 observed reflections (I 〉 2σ(I)). The crystallographic results of molecule 1 show that the functionalized aziridine ring is fused with a lactone ring to form the component with [3.1.0] bicyclic skeleton.
基金by the National Natural Science Foundation of China (No. 29672004).
文摘Chiral butyrolacto[3,4-b]-2(S)-6(R)-1-N-akylaziridines 7 were synthesized in enantiopure form utilizing racemic 5-methoxy-3-bromo-2(5H)-furanone (5) and available amines (6) as key precursors. After highly effective reduction of 7, the functionalized 2(S),3(R)-dihyroxymethyl-N-alkylaziridines (8) were obtained in good yields with ≥98% ee. This is a simple and pratical method for the preparation of enantiopure aziridines which are important interme-diates in the synthesis of biologic active molecules.