Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 26, Pages 7904-7915Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000349
Keywords
boranes; cycloaddition; heterocycles; isocyanides; multicomponent reactions
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Funding
- DGICYT (Spain) [CTQ 2009-07758, SAF2008-05595]
- Generalitat de Catalunya [SGR 2009-249]
- Almirall SA
- Grupo Ferrer (Barcelona)
- DGICYT
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New 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.
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