On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate

Pei Wen Duan, Ching Chen Chiu, Wei Der Lee, Li Shiue Pan, Uppala Venkatesham, Zheng Hao Tzeng, 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

10 引文 斯高帕斯(Scopus)

摘要

The treatment of a range of N- and O-enones derived from various camphor-based chiral auxiliaries A-D with N-aminophthalimide in the presence of lead tetraacetate is described. In general, N-phthalimidoaziridines were obtained with high diastereoselectivities (up to 98% de) and chemical yields (up to 95%) when 10,10-diphenyl-2,10-camphanediol A derived O-enones with a range of substituents were used under the same reaction conditions. Excellent stereoselectivity was obtained when the N-tosyl camphorpyrazolidinone E derived acrylate was used. The absolute configuration of the new stereogenic center(s) of the major diastereomer was established by X-ray crystallographic analysis. Chiral auxiliary cleavage was achieved under mild reaction conditions. A model to explain the stereochemical induction is also proposed.

原文英語
頁(從 - 到)682-690
頁數9
期刊Tetrahedron Asymmetry
19
發行號6
DOIs
出版狀態已發佈 - 2008 四月 3

ASJC Scopus subject areas

  • 催化
  • 物理與理論化學
  • 有機化學
  • 無機化學

指紋

深入研究「On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate」主題。共同形成了獨特的指紋。

引用此