DyKAT by DiCat: Stereoconvergent Dienamine-Catalyzed Claisen Rearrangements
| Autor: | Ana De Oliveira Silva, Jordan L. Harper, Katherine N. Fuhr, Roger A. Lalancette, Paul Ha-Yeon Cheong, Stacey E. Brenner-Moyer |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | The Journal of Organic Chemistry. 87:10105-10113 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | This Claisen rearrangement establishes the feasibility of DyKAT of γ-epimeric enals via dienamine formation to afford enantioenriched products. γ-Aryl and -alkyl enals, and exocyclic enals that introduce quaternary centers, are all amenable substrates. Products are readily converted into pyrrolidines or cyclopentenols. Notably, a reactive dienamine intermediate has been isolated from a catalytic reaction, fully characterized, and converted to product upon reexposure to reaction conditions. Product configuration arises from a directing C-H···π interaction in the transition state. |
| Databáze: | OpenAIRE |
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