Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates
Abstract:
We developed an asymmetric organocatalytic synthesis of 4{,}6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products{,} which are novel bisindole-piperidine-amino acid hybrids{,} can be obtained in one step from 3-vinyl indoles with imino esters in dichloromethane at room temperature after 1 h of reaction time. A variety of these compounds could be synthesized in up to 70% yield and 99% ee{,} and they were experimentally and computationally analyzed regarding their relative and absolute stereochemistry.
| Zugehörige Institution(en) am KIT | Institut für Organische Chemie (IOC) Institut für Toxikologie und Genetik (ITG) |
| Publikationstyp | Zeitschriftenaufsatz |
| Jahr | 2014 |
| Sprache | Englisch |
| Identifikator | ISSN: 1477-0520, 1477-0539 KITopen-ID: 1000046412 |
| HGF-Programm | 47.02.01 (POF II, LK 01) |
| Erschienen in | Organic & biomolecular chemistry |
| Band | 12 |
| Heft | 20 |
| Seiten | 3265-3270 |
| Bemerkung zur Veröffentlichung | RSC geförderter Open Access-Artikel |
| Nachgewiesen in | Scopus Web of Science |