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Pure Appl. Chem., 2013, Vol. 85, No. 4, pp. 741-753

Published online 2013-03-13

Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products

Hee-Yoon Lee*, Seog-Beom Song, Taek Kang, Yoon Jung Kim and Su Jeong Geum

Department of Chemistry, KAIST, Yuseong, Daejeon 305-701, Korea

Abstract: 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 4π 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.