Dichloromethane → n-Phenylisoxazolidin-5-one

반응식

[N:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:2].C[C:10]([O-:13])([CH3:12])C.[K+].[CH2:15](Cl)Cl>>[C:3]1([N:1]2[CH2:15][CH2:12][C:10](=[O:13])[O:2]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

반응물 3

HCID 6344Dichloromethane

HCID 11473Nitrosobenzene

HCID 23665647Potassium tert-butoxide

생성물 1

HCID 68587357n-Phenylisoxazolidin-5-one

실험 절차

Experiments were also conducted by reacting the following α,β-unsaturated aldehydes represented by the formula (II) as defined above, all with nitrosobenzene in the presence of the IPrCl catalyst (10-20 mol %), KOtBu and CH2Cl2 (r.t., 1-6 h) forming the corresponding N-phenylisoxazolidin-5-one derivatives in the following yields a (%, determined by 1H NMR), and then treating the N-phenylisoxazolidin-5-one derivatives with MeOH in the presence of an acid catalyst (r.t., 12 h) forming the corresponding β-amino acid ester derivatives in the following yields b (%): i) R1=3-Br-4-OTfPh and R2═H; yield a=83%; yield b=79%. ii) R1=4-CNPh and R2═H; yield a=95%; yield b=40%. iii) R1═C6F5 and R2═H; yield a=85%; yield b=72%. iv) R1=3,5-F2Ph and R2═H; yield a=88%; yield b=78%. v) R1═C4H9 and R2═H; yield a=40%; yield b=30%.