Stereoselective Synthesis of ( E )- and ( Z )-Isocyanoalkenes
Stereoselective Synthesis of ( E )- and ( Z )-Isocyanoalkenes
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(E)-和(Z)-异氰基烯烃的立体选择性合成
DOI：
10.1021/acs.orglett.2c03461
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发表时间：
2022
期刊：
影响因子：
5.2
通讯作者：
Fleming, Fraser F.
中科院分区：
文献类型：
--
作者：
Tian, Huan;Holyoke, Caleb W.;Fleming, Fraser F.
(E)-通过碘代乙烯与甲酰胺的顺序交叉偶联，然后脱水，选择性地合成了（Z）-异氰基烯烃。由Cu Ⅱ和反式-N，N′-二甲基-1，2-环己二胺原位生成的最佳催化剂可使（E）-或（Z）-乙烯基碘与甲酰胺快速偶联，从而使生成的乙烯基甲酰胺的异构化最小化。该方法有效地提供了一系列的无环，碳环，和杂环的异氰基烯烃;的多功能性与非对映异构体异氰基烯烃抗生素，B371和E-B371的选择性，立体分散合成说明。
(E)- and (Z)-isocyanoalkenes were selectively synthesized via the sequential cross coupling of vinyl iodides with formamide, followed by dehydration. The optimal catalyst, generated in situ from CuII andtrans-N,N′-dimethyl-1,2-cyclohexanediamine, rapidly coupled (E)- or (Z)-vinyl iodides with formamide, which minimized the isomerization of the resultant vinyl formamide. The method efficiently provided a range of acyclic, carbocyclic, and heterocyclic isocyanoalkenes; the versatility is illustrated with the selective, stereodivergent syntheses of the diastereomeric isocyanoalkene antibiotics, B371 andE-B371.