Deng Yongming, Kumar Siddhartha, Wheeler Kraig, Wang Hong
Department of Chemistry and Biochemistry, Miami University, 701 E High Street, Oxford, OH 45056 (USA).
Chemistry. 2015 May 18;21(21):7874-80. doi: 10.1002/chem.201406569. Epub 2015 Apr 15.
A trio catalyst system, composed of arylamine, BINOL-derived phosphoric acid, and Y(OTf)3 , enables the combination of enamine catalysis with both hard metal Lewis acid catalysis and Brønsted acid catalysis for the first time. Using this catalyst system, a three-component aza-Diels-Alder reaction of substituted cinnamaldehyde, cyclic ketone, and arylamine is carried out with high chemo- and enantioselectivity, affording a series of optically active 1,4-dihydropyridine (DHP) derivatives are obtained in 91-99 % ee and 59-84 % yield. DHPs bearing a chiral quaternary carbon center are also obtained with good enantioselectivity and moderate yield (three examples). Preliminary mechanistic investigations have also been conducted.
一种由芳胺、联萘酚衍生的磷酸和Y(OTf)₃组成的三元催化剂体系，首次实现了烯胺催化与硬金属路易斯酸催化和布朗斯特酸催化的结合。使用该催化剂体系，取代肉桂醛、环酮和芳胺的三组分氮杂狄尔斯-阿尔德反应以高化学选择性和对映选择性进行，得到一系列光学活性的1,4-二氢吡啶（DHP）衍生物，对映体过量值为91-99%，产率为59-84%。还获得了具有手性季碳中心的DHP，其对映选择性良好，产率适中（三个例子）。还进行了初步的机理研究。
