N-Heterocyclic Carbene Catalysis: Enantioselective Formal [2+2] Cycloaddition of Ketenes and N-Sulfinylanilines
N-Heterocyclic Carbene Catalysis: Enantioselective Formal [2+2] Cycloaddition of Ketenes and N-Sulfinylanilines
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N-杂环卡宾催化：乙烯酮和 N-亚磺酰苯胺的对映选择性缩甲醛 [2 2] 环加成
DOI：
10.1002/anie.201102488
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发表时间：
2011-01-01
影响因子：
16.6
通讯作者：
Ye, Song
中科院分区：
文献类型：
--
作者：
Jian, Teng-Yue;He, Lin;Ye, Song
作为 β-sultam 和 β-内酰胺的类似物，3-oxo-βsultam（1, 2-thiazetidin-3-one 1, 1-diides）是一类新型四元杂环化合物，具有有趣的生物活性。 [1]然而，据我们所知，还没有关于这些杂环的对映选择性合成的报道。[1a]我们设想，3-氧代-β-磺内酰胺可以通过相应的1, 2-噻嗪丁-3-酮1-氧化物(A)的氧化来轻松合成，[2]可以通过烯酮的[2+2]环加成获得 N-亚磺酰胺（方案 1）。
As analogues of both β-sultams and β-lactams, 3-oxo-βsultams (1, 2-thiazetidin-3-one 1, 1-dioxides), are a novel class of four-membered heterocycles showing interesting biological activities.[1] However, to the best of our knowledge, there is no report for the enantioselective synthesis of these heterocycles.[1a] We envisioned that the 3-oxo-β-sultams could be easily synthesized by oxidation of the corresponding 1, 2-thiazetidin-3-one 1-oxides (A),[2] which could be accessed from the [2+ 2] cycloaddition of ketenes with N-sulfinylamines (Scheme 1).