Badillo Joseph J, Silva-García Abel, Shupe Benjamin H, Fettinger James C, Franz Annaliese K
Department of Chemistry, University of California, One Shields Ave, Davis, California 95616, United States.
Tetrahedron Lett. 2011 Oct 26;52(43):5550-5553. doi: 10.1016/j.tetlet.2011.08.071.
The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-β-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration.
在手性磷酸催化下，异吲哚酮与5-甲氧基色胺之间的缩合环化反应能以优异的产率（高达99%）和对映选择性（高达98:2的对映体过量）得到螺环氧化吲哚四氢-β-咔啉产物。通过对催化剂的比较，可为底物范围以及螺环化反应中高效催化活性和选择性的影响因素提供见解。在联萘体系上具有不同3,3'-取代基且轴向手性相反的手性磷酸，能得到具有相同绝对构型的螺环吲哚酮产物。
