通过有机催化多米诺迈克尔/环化反应高效立体选择性构建 3,3'-吡咯烷二酮螺吲哚啉。
Highly efficient and stereocontrolled construction of 3,3'-pyrrolidonyl spirooxindoles via organocatalytic domino Michael/cyclization reaction.
机构信息
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
出版信息
Org Lett. 2013 Mar 15;15(6):1246-9. doi: 10.1021/ol400183k. Epub 2013 Mar 1.
A wide range of structurally diverse 3,3'-thiopyrrolidonyl spirooxindoles bearing three contiguous stereogenic centers can be smoothly obtained via a domino Michael/cyclization reaction between 3-isothiocyanato oxindoles and 3-methyl-4-nitro-5-alkenyl-isoxazoles with commercially available quinine as the catalyst under mild conditions. The protocol is significantly characterized by high reactivity, a low catalyst loading (1 mol %), and an excellent diastereo- and enantioselectivity (up to >99:1 dr and 98% ee).
一系列结构多样的 3,3'-硫代吡咯烷酮螺吲哚类化合物，它们具有三个连续的立体中心，可以通过 3-异硫氰酸基氧化吲哚和 3-甲基-4-硝基-5-烯基异恶唑之间的多米诺迈克尔/环化反应，在温和条件下，以商业可得的奎宁作为催化剂，顺利地得到。该方案的显著特点是反应活性高，催化剂用量低（1 mol%），对映选择性和非对映选择性极好（高达 >99:1 dr 和 98%ee）。
Zotero 插件