Epoxides and Aziridines

Critical position/factor Effect on carcinogenic potential Rationale 

Substitution at the t if R3 — ethyl or vinyl High alkylating activity 

Position t if at terminal end of alkyl chain J. if interdispersed or attached to a rigid ring Higher molecular flexibility Low/no molecular flexibility 

Functionality t if bifunctional/potentially bifunctional or polyfunctional Cross-linking potential 

---

Epoxides and aziridines are also capable of electrophilic subsitution of indoles. Indolylmagncsium bromide and cyclohexene oxide react to give 3-(lrans-2-hydroxycyclohexyl)indole[14]. Reaction of indoles with epoxides also occurs in the presence of Lewis acids. For example, indole reacts with methyl 2S,3R-epoxybutanoate at C3 with inversion of configuration[15]. 

Catalytic asymmetric epoxidation and aziridination mediated by sulfur ylides 98SL329. 

Asymmetric Synthesis of Epoxides and Aziridines from Aldehydes and I mines... 

This review summarizes the best asymmetric methods for preparing epoxides and aziridines from aldehydes (or ketones) and imines. 

---