[3,3]‐Sigmatropic Rearrangement of Cyclopropenylcarbinyl Cyanates: Access to Alkylidene(aminocyclopropane) Derivatives,Chemistry - A European Journal

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[3,3]‐Sigmatropic Rearrangement of Cyclopropenylcarbinyl Cyanates: Access to Alkylidene(aminocyclopropane) Derivatives
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-09-10 , DOI: 10.1002/chem.201803231
Guillaume Ernouf ₁ , Jean-Louis Brayer ₂ , Benoît Folléas ₂ , Jean-Pierre Demoute ₂ , Christophe Meyer ₁ , Janine Cossy ₁

Affiliation

Cyclopropenylcarbinyl cyanates, generated in situ by dehydration of the corresponding carbamates, underwent an efficient and stereoselective [3,3]‐sigmatropic rearrangement leading to the corresponding alkylidene(isocyanatocyclopropanes), which could be converted into various alkylidene(aminocyclopropane) derivatives in a one‐pot manner. This transformation complements the repertoire of sigmatropic rearrangements involving cyclopropenylcarbinol derivatives and in particular, the previously reported Overman rearrangement of cyclopropenylcarbinyl trichloroacetimidates.

中文翻译：

[3,3]-环丙烯基羰基氰基酸酯的正向重排：获得亚炔基（氨基环丙烷）衍生物

通过相应的氨基甲酸酯脱水原位生成的环丙烯基羰基氰酸酯，经过高效且立体选择性的[3,3]-σ重排，导致相应的亚烷基（异氰酸根合环丙烷），可以将其转化为多种亚烷基（氨基环丙烷）衍生物。锅方式。这种转变补充了涉及环丙烯基甲醇衍生物的σ重排的所有组成，特别是先前报道的环丙烯基羰基三氯乙酰亚胺酸酯的超人重排。

更新日期：2018-09-10

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