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Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Abbasov, Mikail E. Hudson, Brandi M. Kong, Weixu Tantillo, Dean J. Romo, Daniel |
| Copyright Year | 2017 |
| Abstract | α,β-Unsaturated acylammonium salts are useful dienophiles enabling highly enantioselective and stereodivergent Diels-Alder-initiated organocascades with furan-based dienes. Complex polycyclic systems can thus be obtained from readily prepared dienes, commodity acid chlorides, and a chiral isothiourea organocatalyst under mild conditions. We describe the use of furan-based dienes bearing pendant sulfonamides leading to the generation of oxa-bridged, trans-fused tricyclic γ-lactams. This process constitutes the first highly enantio- and diastereoselective, organocatalytic Diels-Alder cycloadditions with these typically problematic dienes due to their reversibility. Computational studies suggest that the high diastereoselectivity with these furan dienes may be due to a reversible Diels-Alder cycloaddition for the endo adducts. In addition, the utility of this methodology is demonstrated through a concise approach to a core structure with similarity to the natural product isatisine A and a nonpeptidyl ghrelin-receptor inverse agonist. |
| Starting Page | 3179 |
| Ending Page | 3183 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c6ob02738e |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/c6/ob/c6ob02738e/c6ob02738e1.pdf |
| PubMed reference number | 28358148 |
| Alternate Webpage(s) | https://doi.org/10.1039/c6ob02738e |
| Journal | Medline |
| Volume Number | 15 |
| Issue Number | 15 |
| Journal | Organic & biomolecular chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
