Lewis-Acid-Mediated Thiocyano Semipinacol Rearrangement of Allylic Alcohols for Construction of α-Quaternary Center β-Thiocyano Carbonyls,Organic Letters

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Lewis-Acid-Mediated Thiocyano Semipinacol Rearrangement of Allylic Alcohols for Construction of α-Quaternary Center β-Thiocyano Carbonyls
Organic Letters ( IF 4.9 ) Pub Date : 2019-11-19 , DOI: 10.1021/acs.orglett.9b03722
Xu-Feng Song ₁ , Ai-Hui Ye ₁ , Yu-Yang Xie ₁ , Jia-Wei Dong ₁ , Chao Chen ₁ , Ye Zhang ₁ , Zhi-Min Chen ₁

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An electrophilic thiocyano semipinacol rearrangement of allylic alcohols has been achieved for the first time by using N-thiocyano-dibenzenesulfonimide (NTSI). This approach provides a direct, simple, and efficient strategy for the formation of thiocyano carbonyl compounds with moderate to excellent yields. Meanwhile, an all-carbon quaternary center was rapidly constructed. In addition, an asymmetric version of this tandem reaction was preliminarily investigated.

中文翻译：

Lewis酸介导的烯丙醇的硫氰酸氰基频哪醇重排用于构建α-季中心β-硫氰基羰基。

通过使用N-硫氰基-二苯磺酰亚胺（NTSI），首次实现了烯丙基醇的亲电子硫氰基半频醇重排。该方法提供了直接，简单和有效的策略，以中等至极好的收率形成硫氰基羰基化合物。同时，全碳四元中心建设迅速。另外，初步研究了该串联反应的不对称形式。

更新日期：2019-11-20

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