Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.,Chemical Science

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Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.
Chemical Science ( IF 7.6 ) Pub Date : 2019-10-08 , DOI: 10.1039/c9sc03790j
Bastian Muriel ₁ , Alec Gagnebin ₁ , Jerome Waser ₁

Affiliation

We report the convergent synthesis of bicyclo[3.1.0]hexanes possessing an all-carbon quaternary center via a (3 + 2) annulation of cyclopropenes with cyclopropylanilines. Using an organic or an iridium photoredox catalyst and blue LED irradiation, good yields were obtained for a broad range of cyclopropene and cyclopropylaniline derivatives. The reaction was highly diastereoselective when using difluorocyclopropenes together with a removable substituent on the cyclopropylaniline, giving access to important building blocks for medicinal chemistry. With efficient methods existing for the synthesis of both reaction partners, our method grants a fast access to highly valuable bicyclic scaffolds with three contiguous stereocenters.

中文翻译：

通过环丙烯与氨基环丙烷的 (3 + 2) 环化合成双环[3.1.0]己烷。

我们报道了通过环丙烯与环丙基苯胺的（3 + 2）环化，收敛合成具有全碳四元中心的双环[3.1.0]己烷。使用有机或铱光氧化还原催化剂和蓝色 LED 照射，多种环丙烯和环丙基苯胺衍生物均获得了良好的收率。当使用二氟环丙烯与环丙基苯胺上的可去除取代基时，该反应具有高度非对映选择性，从而获得了药物化学的重要组成部分。利用现有的合成两种反应伙伴的有效方法，我们的方法可以快速获得具有三个连续立体中心的高价值双环支架。

更新日期：2019-11-28

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