Aziridinyl Imines in Organic Synthesis: Development of Tandem Reaction Strategies and Application to Total Synthesis of Natural Products
- Aziridinyl Imines in Organic Synthesis: Development of Tandem Reaction Strategies and Application to Total Synthesis of Natural Products
- 강택; 이희윤; 송석범; 김윤정; 금수정
- Issue Date
- Pure and applied chemistry. : Chimie pure et appliqueé
- VOL 85, NO 4-753
- Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4 pi system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.
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