Asymmetric Quadruple Aminocatalytic Domino Reactions to Fused Carbocycles Incorporating a Spirooxindole Motif

The efficient assembly of hydroindane derivatives incorporating a spirooxindole motif was realized via a new three-component domino reaction of (E)-4-(1-methyl-2-oxoindolin-3-ylidene)-3-oxobutanoates and two molecules of α,β-unsaturated aldehydes under quadruple iminium−enamine−iminium−enamine catalysis. The complex products bearing six contiguous stereogenic centers were obtained in excellent stereoselectivities (96−>99% ee, >99% de).

通过(E)-4-(1-甲基-2-氧代吲哚啉-3-亚基)-3-氧代丁酸酯与两分子α,β-不饱和醛参与的新型三组分多米诺反应，在四重亚胺鎓-烯胺-亚胺鎓-烯胺催化体系下，成功实现了含螺吲哚酮（spirooxindole）骨架的氢化茚衍生物的高效构建。所得复杂产物带有六个连续手性中心，且均以优异的立体选择性获得，其对映体过量值为96%~>99% ee，非对映体过量值>99% de。