Highly diastereo- and enantioselective direct aldol reactions promoted by water-compatible organocatalysts bearing a pyrrolidinyl-camphor structural scaffold

Zheng Hao Tzeng, Hung Yao Chen, Raju Jannapu Reddy, Ching Ting Huang, Kwunmin Chen*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

59 引文 斯高帕斯(Scopus)

摘要

Efficient synthetic routes have been developed for the synthesis of a series of pyrrolidinyl-camphor containing organocatalysts (1-10). Structural modifications were made by varying the stereo- and electronic properties of the camphor scaffold and the aromatic substituents. These readily tunable and amphiphilic organocatalysts were evaluated for the direct asymmetric aldol reaction of various aromatic aldehydes and cyclohexanone either in organic solvents or in the presence of water. The aldol reaction proceeded smoothly with excellent chemical yields (up to 99%), enantioselectivities (up to 99% ee), and anti-diastereoselectivities (up to 99:1) with a catalytical amount of the bifunctional organocatalysts (20 mol %) under optimal reaction conditions. Mechanistic transition models are proposed and the stereochemical bias of the asymmetric aldol reaction is presented.

原文英語
頁(從 - 到)2879-2888
頁數10
期刊Tetrahedron
65
發行號15
DOIs
出版狀態已發佈 - 2009 四月 11

ASJC Scopus subject areas

  • 生物化學
  • 藥物發現
  • 有機化學

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