Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; Shanghai Key Laboratory of New Drug Design, School of Pharmacy, ‡State Key Laboratory of Chemical Engineering, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
Org Lett. 2017 May 5;19(9):2322-2325. doi: 10.1021/acs.orglett.7b00862. Epub 2017 Apr 26.
The first example of a photoexcitated amine-catalyzed process for asymmetric Michael addition of o-quinodimethanes to enones is described. In the presence of simple chiral amino acid esters, a variety of Michael adducts were generally obtained in good yields and excellent stereoselectivities. This strategy can be successfully applied to 3-substituted-2-cyclohexenones and provides an asymmetric access to all-carbon quaternary centers. Furthermore, the high stereocontrol was explained by means of density-functional theory (DFT) calculations.
首例光激发的胺催化的对醌二甲基烷与烯酮的不对称迈克尔加成反应被描述。在简单的手性氨基酸酯存在下，多种迈克尔加成产物通常以良好的收率和优异的立体选择性得到。该策略可以成功应用于 3-取代的 2-环己烯酮，并为全碳季碳中心提供了一种不对称的方法。此外，通过密度泛函理论（DFT）计算解释了高立体控制。
