Catalytic Asymmetric Mannich/Cyclization of 2-Isothiocyanato-1-indanones: An Approach to the Synthesis of Bispirocyclic Indanone–Thioimidazolidine–Oxindoles,Organic Letters

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Catalytic Asymmetric Mannich/Cyclization of 2-Isothiocyanato-1-indanones: An Approach to the Synthesis of Bispirocyclic Indanone–Thioimidazolidine–Oxindoles
Organic Letters ( IF 4.9 ) Pub Date : 2018-06-20 00:00:00 , DOI: 10.1021/acs.orglett.8b01389
Bo-Liang Zhao ₁ , Da-Ming Du ₁

Affiliation

This study demonstrates that novel isothiocyanates derived from 1-indanones are useful building blocks in heteroannulation reactions with isatinimines. This convenient Mannich/cyclization cascade reaction serves as a powerful tool for the enantioselective construction of bispirocyclic indanone–thioimidazolidine–oxindoles bearing two adjacent spiro-quaternary stereocenters in good to excellent yields with excellent diastereo- and enantioselectivities. Versatile transformations of the products into other potential bioactive bispirocyclic heterocycles have also been demonstrated.

中文翻译：

催化不对称曼尼希/ 2-异硫氰酸根-1-茚满酮的环化：双螺环茚满酮-硫咪唑烷-辛醇合成的一种方法

这项研究表明，衍生自1-indanones的新型异硫氰酸酯是与isatinimines异环反应中的有用组成部分。这种方便的曼尼希/环化级联反应可作为具有两个相邻的螺-季立体中心的双螺环茚满酮-硫代咪唑烷-氧吲哚的对映选择性构建的有力工具，并具有优异的非对映和对映选择性，且收率很高。还已经证明了产物向其他潜在的生物活性双螺环杂环的多功能转化。

更新日期：2018-06-20

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