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Enantioselective Construction of Quaternary N-Heterocycles by Palladium-Catalyzed Decarboxylative Allylic Alkylation of Lactams
| Content Provider | PubMed Central |
|---|---|
| Author | Behenna, Douglas C. Liu, Yiyang Taiga, Yurino Kim, Jimin White, David E. Virgil, Scott C. Stoltz, Brian M. |
| Abstract | The enantioselective synthesis of Nitrogen-containing heterocycles (N-heterocycles) represents a substantial chemical research effort and resonates across numerous disciplines including the total synthesis of natural products and medicinal chemistry. In this manuscript, we describe the highly enantioselective palladium-catalyzed decarboxylative allylic alkylation of readily available lactams to form 3,3,-disubstituted pyrrolidinones, piperidinones, caprolactams, and structurally related lactams. Given the prevalence of quaternary N-heterocycles in biologically active alkaloids and pharmaceutical agents, we envision that our method will provide a synthetic entry into the de novo asymmetric synthesis of such structures. As an entry for these investigations we demonstrate how the described catalysis affords enantiopure quaternary lactams that intercept synthetic intermediates previously employed in the synthesis of the Aspidosperma alkaloids quebrachamine and rhazinilam, but that were previously only available by chiral auxiliary approaches or as racemic mixtures. |
| Related Links | http://dx.doi.org/10.1038/nchem.1222 |
| Ending Page | 133 |
| Page Count | 4 |
| Starting Page | 130 |
| File Format | |
| ISSN | 17554330 |
| e-ISSN | 17554349 |
| Journal | Nature chemistry |
| Issue Number | 2 |
| Volume Number | 4 |
| Language | English |
| Publisher Date | 2011-12-01 |
| Access Restriction | Open |
| Subject Keyword | Chemistry(all) Chemical Engineering(all) Research in Higher Education |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry Chemical Engineering |
