Ring-opening of cis-3-Substituted-2-vinylaziridines with Heteroatom Nucleophiles

摘要

Aziridines have been used as key intermediates for the synthesis of many nitrogen-containing natural products and biologically active compounds. The chemical transformation caused by ring-opening with nucleophiles is the main synthetic utility of aziridines.1 Vinylaziridines, classified as fiinctionalized aziridines, have been considered to be increasingly attractive building blocks in organic synthesis.2 Although unsubstituted 2-vinylaziridines have been targets for intense synthetic applications, 3-substututed-2-vinylaziridines as synthetic intermediates have relatively not been studied much. During the course of our synthetic studies on oseltamivir phosphate (Tamiflu), we utilized the ring-opening reaction of aziridines that contain the czs-3-substituted-2-vinylaziri-dine structure as a core step, which proceeded with excellent regio-and stereoselectivity (eq. I).3 Aziridine 1, containing an alkenyl aziridine moiety, was attacked by 3-pentanol in a regio-and stereoselective fashion to exclusively afford the desired product.