Assembly of Indolenines, 3-Amino Oxindoles, and Aldehydes into Indolenine-Substituted Spiro[pyrrolidin-2,3′-oxindoles] via 1,3-Dipolar Cycloaddition with Divergent Diastereoselectivities
作者:Guodong Zhu、Siyuan Liu、Shiqi Wu、Lianghong Peng、Jingping Qu、Baomin Wang
DOI:10.1021/acs.joc.7b00316
日期:2017.4.21
A novel one-pot 1,3-dipolar cycloaddition of indolenines, 3-aminooxindoles, and aldehydes is reported. The reaction provides indolenine-substituted spiro[pyrrolidin-2,3′-oxindoles] containing four contiguous stereogenic centers in high yields (up to 99%) and excellent diastereoselectivities (up to >20:1 dr) under mild conditions. Remarkably, the inversion of diastereoselectivity could be readily achieved
报道了吲哚,3-氨基羟吲哚和醛的新型一锅式1,3-偶极环加成反应。该反应在温和条件下提供了高产率(最高达99%)和四个非对映选择性(最高达> 20:1 dr)的吲哚烯基取代的螺[吡咯烷-2,3'-羟吲哚],其中包含四个连续的立体异构中心。值得注意的是,通过稍微改变反应条件可以容易地实现非对映选择性的转化。