Cioc Răzvan C, Estévez Verónica, van der Niet Daan J, Vande Velde Christophe M L, Turrini Nikolaus G, Hall Mélanie, Faber Kurt, Ruijter Eelco, Orru Romano V A
Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS) Vrije Universiteit Amsterdam De Boelelaan 1108 1081 HZ Amsterdam The Netherlands.
Faculty of Applied Engineering University of Antwerp Groenenborgerlaan 171 2020 Antwerpen Belgium.
European J Org Chem. 2017 Mar 3;2017(9):1262-1271. doi: 10.1002/ejoc.201601432. Epub 2017 Mar 8.
We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product - the α-carboxamido lactone - into an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis.
我们报道了双功能起始原料（酮酸）在非对映选择性Passerini三中心-双组分反应中的应用。对反应范围的研究揭示了异腈加成中立体选择性所需的结构特征。在该体系中，发现伯Passerini产物——α-羧酰胺内酯——在酸性条件下会发生有趣的异构化，生成一种非典型产物α-羟基酰亚胺。此外，对映体富集的Passerini产物可由通过化学酶法合成得到的对映体富集的酮酸生成。
