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Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Taylor, Laura L. Goldberg, Frederick W. Hii, King Kuok Mimi |
| Copyright Year | 2012 |
| Abstract | An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis. |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c2ob25122a |
| PubMed reference number | 22565504 |
| Journal | Medline |
| Volume Number | 10 |
| Issue Number | 22 |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/ob/c2/c2ob25122a/c2ob25122a.pdf |
| Alternate Webpage(s) | http://spiral.imperial.ac.uk/bitstream/10044/1/11207/4/OBC2012v10p4424.pdf |
| Alternate Webpage(s) | https://doi.org/10.1039/c2ob25122a |
| Journal | Organic & biomolecular chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |