Add time:07/19/2019         Source:sciencedirect.com

Publisher SummaryThis chapter provides information on three-membered ring systems. The chemistry of three-membered rings continues to be as exciting, owing to the enormous synthetic utility of these compounds. The chapter presents the discussion from a synthetic chemist's point of view, with an eye towards new understanding of existing methods, and new applications and techniques. The chapter presents a discussion on the preparation and reaction of epoxides and aziridines. Epoxides can be prepared through one of two broadly defined methods: introduction of an oxygen atom to an existing alkene (approach a), or by modification of a carbonyl substrate (approach b), whereby the former approach is the more familiar. The chiral salen catalysts developed by Jacobsen and Katsuki find frequent use, and convenient methods for their industrial preparation continues to be reported. The most familiar reaction of epoxides is their propensity to undergo ring-opening with various nucleophiles. In the area of imine functionalization, aziridines can be synthesized enantioselectively from imines and alkyl halides using a camphor-derived chiral sulfide mediator in a one-pot procedure via the imino Corey–Chaykovsky reaction. Aziridines can also be formed by the ring closure of appropriately substituted amines. Aziridines can undergo a variety of conversions, which provide new heterocyclic species.

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