In this work,six novel axially unfixed biaryl-based water-compatible bifunctional organocatalysts were de-signed and synthesized for the organocatalytic access to a variety of 3-alkyl-3-hydroxy-2-oxindole derivatives ...In this work,six novel axially unfixed biaryl-based water-compatible bifunctional organocatalysts were de-signed and synthesized for the organocatalytic access to a variety of 3-alkyl-3-hydroxy-2-oxindole derivatives via aldol reactions in water.Organocatalyzed by 5a,the direct aldol reactions of isatins with enolisable ketones under-went readily in water,furnishing the structurally diverse 3-alkyl-3-hydroxy-2-oxindoles in various stereoselectivi-ties(up to>99%dr and>99%ee).Moreover,a plausible transition state of the conducted aldol reactions was hy-pothesized to shed light on the observed stereoselectivities of the obtained 3-alkyl-3-hydroxy-2-oxindoles.展开更多
基金We thank the Beijing Municipal Commission of Education(No.JC015001200902)the Beijing Municipal Natural Science Foundation(Nos.710201,2122008)+1 种基金the Basic Research Foundation of Beijing University of Technology(No.X4015001201101)the Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of Beijing Municipality(No.PHR201008025)and the Doctoral Scientific Research Start-up Foundation of Beijing University of Technology(No.52015001200701)for financial supports.
文摘In this work,six novel axially unfixed biaryl-based water-compatible bifunctional organocatalysts were de-signed and synthesized for the organocatalytic access to a variety of 3-alkyl-3-hydroxy-2-oxindole derivatives via aldol reactions in water.Organocatalyzed by 5a,the direct aldol reactions of isatins with enolisable ketones under-went readily in water,furnishing the structurally diverse 3-alkyl-3-hydroxy-2-oxindoles in various stereoselectivi-ties(up to>99%dr and>99%ee).Moreover,a plausible transition state of the conducted aldol reactions was hy-pothesized to shed light on the observed stereoselectivities of the obtained 3-alkyl-3-hydroxy-2-oxindoles.
