On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones: The conformational analysis of camphor derived N- and O-enones

Wei Der Lee, Ching Chen Chiu, Hua Lin Hsu, 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

18 引文 斯高帕斯(Scopus)

摘要

Various camphor derived N- and O-enones were treated with selected oxidants to provide the corresponding epoxides in a wide range of diastereoselectivity. For camphorsultam derived activated alkenes, high to excellent stereoselectivities were obtained when the s-trans enones were treated with methyl(trifluoromethyl)dioxirane. On the other hand, for exo-10,10-diphenyl-2, 10-camphanediol (3) and exo-10,10-diphenyl-10-methoxy-2-camphanol (4) derived alkenes, the use of s-cis enones gave the desired epoxide with excellent diastereoselectivity under the same reaction conditions. The stereoselectivity was highly dependent on the geometry of the auxiliaries derived enones and the stereochemical induction is discussed.

原文英語
頁(從 - 到)6657-6664
頁數8
期刊Tetrahedron
60
發行號31
DOIs
出版狀態已發佈 - 2004 七月 26

ASJC Scopus subject areas

  • 生物化學
  • 藥物發現
  • 有機化學

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