Asymmetric conjugate addition of oxindoles to 2-chloroacrylonitrile: A highly effective organocatalytic strategy for simultaneous construction of 1,3-nonadjacent stereocenters leading to chiral pyrroloindolines

Li X.; Luo S.; Cheng J.-P.

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Asymmetric conjugate addition of oxindoles to 2-chloroacrylonitrile: A highly effective organocatalytic strategy for simultaneous construction of 1,3-nonadjacent stereocenters leading to chiral pyrroloindolines

机译：羟吲哚向2-氯丙烯腈的不对称共轭加成：一种高效的有机催化策略，可同时构建1,3-不相邻的立体中心，从而导致手性吡咯并吲哚啉

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Chiral pyrroloindoles: A highly enantioselective catalytic conjugate addition of 3-substituted oxindoles with 2-chloroacrylonitrile has been developed with a readily accessible alkyl bifunctional tertiary amine thiourea catalyst. Excellent stereoselectivity of up to >30:1 diastereomeric ratio and 99% enantiomeric excess was achieved. The obtained Michael products could be easily converted to chiral pyrroloindole structures, which are widely distributed in natural indole alkaloids (see scheme).

机译：手性吡咯并吲哚：已经开发出具有容易获得的烷基双官能叔胺硫脲催化剂的3-取代的羟吲哚与2-氯丙烯腈的高对映选择性催化共轭加成物。获得了高达> 30：1的非对映异构体比例和99％对映体过量的出色立体选择性。获得的迈克尔产物可以容易地转化为手性吡咯并吲哚结构，其广泛分布于天然吲哚生物碱中（参见方案）。

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《Chemistry: A European journal》 |2010年第48期|共5页
作者
Li X.; Luo S.; Cheng J.-P.;
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正文语种 eng
中图分类应用化学;
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Michael addition; natural products; organocatalysis; oxindoles; quaternary center;

机译：迈克尔加成天然产物有机催化吲哚四元中心;

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1. Asymmetric conjugate addition of oxindoles to 2-chloroacrylonitrile: A highly effective organocatalytic strategy for simultaneous construction of 1,3-nonadjacent stereocenters leading to chiral pyrroloindolines [J] . Li X., Luo S., Cheng J.-P. Chemistry: A European journal . 2010,第48期

机译：羟吲哚向2-氯丙烯腈的不对称共轭加成：一种高效的有机催化策略，可同时构建1,3-不相邻的立体中心，从而导致手性吡咯并吲哚啉
2. Asymmetric organocatalytic conjugate addition of dialkyl phosphites to N-unprotected isatylidene malononitriles: access to 3-phospho-2-oxindoles with chiral quaternary stereocenters [J] . Zhao-Min Liu, Nai-Kai Li, Xiao-Fei Huang, Tetrahedron . 2014,第14期

机译：亚磷酸二烷基酯向N-未保护的异亚丙基丙二腈的不对称有机催化共轭加成：获得具有手性四级立体中心的3-磷酸-2-氧吲哚
3. Asymmetric organocatalytic conjugate addition of dialkyl phosphites to N-unprotected isatylidene malononitriles: access to 3-phospho-2-oxindoles with chiral quaternary stereocenters [J] . Zhao-Min Liu, Nai-Kai Li, Xiao-Fei Huang, Tetrahedron . 2014,第14期

机译：亚磷酸二烷基酯向N-未保护的异亚丙基丙二腈的不对称有机催化共轭加成：获得具有手性四级立体中心的3-磷酸-2-氧吲哚
4. From the Cover: Asymmetric Catalysis Special Feature Part I: Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B [O] . Joel F. Austin, Sung-Gon Kim, Christopher J. Sinz, 2004

机译：从封面开始：不对称催化专刊第I部分：通过级联加成环化策略对吡咯并吲哚进行对映体选择性的有机催化：（-）-氟stramine B的合成
5. Asymmetric construction of quaternary stereocenters by direct conjugate addition of oxindoles to enone [O] . Sun W, Hong L, Liu C, 2010

机译：通过将羟吲哚直接共轭添加到烯酮中来构筑四元立体中心

Asymmetric conjugate addition of oxindoles to 2-chloroacrylonitrile: A highly effective organocatalytic strategy for simultaneous construction of 1,3-nonadjacent stereocenters leading to chiral pyrroloindolines

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