Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates
Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates
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DOI：
10.1021/acs.joc.9b03098
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发表时间：
2020-01-17
影响因子：
3.6
通讯作者：
Ivanova, Olga A.
中科院分区：
文献类型：
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作者：
Boichenko, Maksim A.;Andreev, Ivan A.;Ivanova, Olga A.
以三甲基氰硅烷为氰根离子的替代物，在B（C_6 F_5）（3）或三氟甲磺酸催化下，对给体-受体环丙烷进行开环反应。该方法提供了一个短的路线，γ-氰基酯，可以是有用的合成中间体，用于合成不同的生物活性分子，如谷氨酸和δ-氨基戊酸衍生物，3-芳基哌啶，或其他取代的苯乙胺。相反，在典型的S（N）2条件下，通过环丙烷与氰化钠直接反应合成这些γ-氰基酯的尝试导致形成2-芳基丁二腈。
A straightforward method for ring opening of donor-acceptor cyclopropanes with trimethylsilyl cyanide as a surrogate of cyanide ion in the presence of B(C6F5)(3) or trifluoromethanesulfonic acid as a catalyst has been developed. The methodology provides a short route to gamma-cyanoesters that can be useful synthetic intermediates for the synthesis of diverse bioactive molecules such as glutaric and delta-aminovaleric acid derivatives, 3-arylpiperidines, or other substituted phenethylamines. Oppositely, the attempts to synthesize these gamma-cyanoesters by direct reaction of cyclopropanes with sodium cyanide under typical S(N)2 conditions led to the formation of 2-arylsuccinonitriles.