Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid , 28040-Madrid, Spain.
J Org Chem. 2013 Oct 18;78(20):10154-65. doi: 10.1021/jo4015358. Epub 2013 Oct 2.
The organocatalyzed U-3CR of 4-oxoazetidine-2-carbaldehydes has been studied. In addition, the organocatalyzed P-3CR of 4-oxoazetidine-2-carbaldehydes and azetidine-2,3-diones has been described for the first time. U-3CR and P-3CR adducts have been obtained in good yields and reasonable diastereoselectivities. Phenyl phosphinic acid has been the catalyst of choice to study the scope of both organocatalyzed multicomponent reactions using a variety of β-lactams, isocyanides, and amines. Highly functionalized U-3CR and P-3CR adducts derived from β-lactams have proved to be useful substrates for the preparation of enantiopure γ-lactams and γ-lactones via N1-C2 β-lactam ring opening/cyclization under acidic or basic conditions.
已研究了 4-氧代氮杂环丁烷-2-醛的有机催化 U-3CR。此外，还首次描述了 4-氧代氮杂环丁烷-2-醛和氮杂环丁烷-2,3-二酮的有机催化 P-3CR。U-3CR 和 P-3CR 加合物以良好的收率和合理的非对映选择性获得。苯膦酸已被选为催化剂，用于研究使用各种β-内酰胺、异氰化物和胺的多种有机催化多组分反应的范围。从β-内酰胺衍生而来的高度官能化的 U-3CR 和 P-3CR 加合物已被证明是通过酸性或碱性条件下 N1-C2β-内酰胺开环/环化制备对映纯γ-内酰胺和γ-内酯的有用底物。
