Enhancing the scope of the Diels-Alder reaction through isonitrile chemistry: Emergence of a new class of acyl-activated dienophiles Journal Article
| Authors: | Townsend, S. D.; Wu, X.; Danishefsky, S. J. |
| Article Title: | Enhancing the scope of the Diels-Alder reaction through isonitrile chemistry: Emergence of a new class of acyl-activated dienophiles |
| Abstract: | α,β-Unsaturated imides, formylated at the nitrogen atom, comprise a new and valuable family of dienophiles for servicing Diels-Alder reactions. These systems are assembled through extension of recently discovered isonitrile chemistry to the domain of α,β-unsaturated acids. Cycloadditions are facilitated by Et 2AlCl, presumably via chelation between the two carbonyl groups of the N-formyl amide. Applications of the isonitrile/Diels-Alder logic to the IMDA reaction, as well as methodologies to modify the N-formyl amide of the resultant cycloaddition product, are described. It is expected that this easily executed chemistry will provide a significant enhancement for application of Diels-Alder reactions to many synthetic targets. © 2012 American Chemical Society. |
| Keywords: | methodology; chemistry; molecular structure; diels-alder reaction; dienophiles; diels alder reaction; nitriles; isonitriles; isonitrile derivative; chelation; amides; cycloaddition; acylation; cycloadditions; nitrogen atom; carbonyl groups; cycloaddition products; unsaturated acids; unsaturated imides |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 134 |
| Issue: | 25 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2012-06-27 |
| Start Page: | 10659 |
| End Page: | 10663 |
| Language: | English |
| DOI: | 10.1021/ja303876e |
| PROVIDER: | scopus |
| PMCID: | PMC3396883 |
| PUBMED: | 22708980 |
| DOI/URL: | |
| Notes: | --- - "Export Date: 1 August 2012" - "CODEN: JACSA" - "Source: Scopus" |
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