采用普林斯串联策略立体选择性合成螺[四氢吡喃-3,3'-氧化吲哚]衍生物
Stereoselective synthesis of spiro[tetrahydropyran-3,3'-oxindole] derivatives employing Prins cascade strategy.
作者信息
Reddy B V Subba, Swathi V, Swain Manisha, Bhadra Manika Pal, Sridhar B, Satyanarayana D, Jagadeesh B
机构信息
Natural Product Chemistry, ‡Centre for Chemical Biology, §Laboratory of Crystallography, and ⊥Centre for Nuclear Magnetic Resonance and Structural Chemistry, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad 500 607, India.
出版信息
Org Lett. 2014 Dec 19;16(24):6267-9. doi: 10.1021/ol503089m. Epub 2014 Dec 8.
A variety of aldehydes undergo smooth coupling with 4-hydroxy-N-methyl-2-methylene-N-phenylbutanamide in the presence of BF3·OEt2 under ambient conditions to produce the corresponding spiro-oxindole derivatives in good yields with excellent selectivity. It is an entirely new strategy to construct the spirocycles in a one-pot operation through a Prins cascade process.
在环境条件下，多种醛在三氟化硼乙醚（BF3·OEt2）存在下与4-羟基-N-甲基-2-亚甲基-N-苯基丁酰胺顺利发生偶联反应，以良好的产率和优异的选择性生成相应的螺环氧化吲哚衍生物。这是一种通过普林斯级联反应一锅法构建螺环的全新策略。
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