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Boron-Based Dipolar Multicomponent Reactions: Simple Generation of Substituted Aziridines, Oxazolidines and Pyrrolidines

Posted June 8th, 2010 by pschmidtke
TitleBoron-Based Dipolar Multicomponent Reactions: Simple Generation of Substituted Aziridines, Oxazolidines and Pyrrolidines
Publication TypeJournal Article
Year of Publication2010
AuthorsKielland, N, Catti F, Bello D, Isambert N, Soteras I, Luque FJ, Lavilla R
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Date Published2010/05/27/
AbstractNew multicomponent reactions of aldehydes, isocyanides, trialkylboron reagents and dipolarophiles have been developed as an efficient route to diverse scaffolds, including aziridines, oxazolidines and poly-substituted pyrrolidines. This chemistry, inspired by a report by Hesse in 1965, is simple and involves mild conditions. Computational studies provide a basis to investigate the stereochemical features observed in the formation of oxazolidines and four-component adducts, and permit identification of potential factors that might influence the outcome of the multicomponent reaction. Thus, a rational screening of all the components and reaction parameters is made to examine the manifold mechanistic pathways and establish the practical limits for standard applications. Finally, intramolecular and solid-supported versions of these reactions bring new synthetic possibilities and practical protocols. Overall, the results describe a new family of multicomponent reactions valuable not only for organic reactivity, but also for combinatorial chemistry and drug discovery.