Zaretsky Serge, Adachi Shinya, Rotstein Benjamin H, Hickey Jennifer L, Scully Conor C G, St Denis Jeffrey D, Courtemanche Rebecca, Yu Joy C Y, Chung Benjamin K W, Yudin Andrei K
Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
J Org Chem. 2014 Nov 7;79(21):9948-57. doi: 10.1021/jo5018316. Epub 2014 Oct 22.
The factors determining diastereoselectivity observed in the multicomponent conversion of amino acids, aziridine aldehyde dimers, and isocyanides into chiral piperazinones have been investigated. Amino acid-dependent selectivity for either trans- or cis-substituted piperazinone products has been achieved. An experimentally determined diastereoselectivity model for the three-component reaction driven by aziridine aldehyde dimers has predictive value for different substrate classes. Moreover, this model is useful in reconciling the previously reported observations in multicomponent reactions between isocyanides, α-amino acids, and monofunctional aldehydes.
已对在氨基酸、氮杂环丙烷醛二聚体和异腈多组分转化为手性哌嗪酮过程中观察到的非对映选择性的决定因素进行了研究。已实现了对反式或顺式取代哌嗪酮产物的氨基酸依赖性选择性。由氮杂环丙烷醛二聚体驱动的三组分反应的实验确定的非对映选择性模型对不同底物类别具有预测价值。此外，该模型有助于协调先前报道的异腈、α-氨基酸和单官能醛之间多组分反应中的观察结果。
