Department of Chemistry and Biochemistry, North Dakota State University, Fargo, North Dakota 58108, USA.
Chem Commun (Camb). 2016 Jul 7;52(53):8305-8. doi: 10.1039/c6cc02962k. Epub 2016 Jun 14.
Atropisomeric maleimides were synthesized and subjected to atropselective [5+2]-photocycloaddition under direct irradiation to yield azepinone products with high enantio- (ee >98%) and diastereoselectivity (dr >98%). While the ee was dictated by the axial chirality, the dr was influenced by the substituent on the maleimide ring. Interestingly, by tuning the electronics of the substituent, the dr of the product can be reversed.
手性马来酰亚胺被合成，并在直接照射下进行[5+2]-光环加成反应，以高产率（ee>98%）和高非对映选择性（dr>98%）得到氮杂环庚酮产物。ee 由轴向手性决定，而 dr 则受马来酰亚胺环上取代基的影响。有趣的是，通过调整取代基的电子性质，可以反转产物的 dr。
