A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes.

A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes.
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DOI:
10.1002/anie.201608534
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发表时间:
2016-10-24
影响因子:
16.6
通讯作者:
Smith, Martin D.
Smith, Martin D.
中科院分区:
化学1区
文献类型:
--
作者:
Kiss, Emily;Campbell, Craig D.;Driver, Russell W.;Jolliffe, John D.;Lang, Rosemary;Sergeieva, Tetiana;Okovytyy, Sergiy;Paton, Robert S.;Smith, Martin D.

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分子内Diels-Alder反应的一种方法导致了由三个稠环和多达五个立体中心组成的复杂碳环的级联合成,具有完全的立体控制。计算分析表明,该反应是通过Michael/Michael/环丙烷化/差向异构化级联进行的,其中,反式异构体的大小和配位是关键。
An approach to the intramolecular Diels–Alder reaction has led to a cascade synthesis of complex carbocycles composed of three fused rings and up to five stereocenters with complete stereocontrol. Computational analysis reveals that the reaction proceeds by a Michael/Michael/cyclopropanation/epimerization cascade in which size and coordination of the counterion is key.
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