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Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates

Zhong, Sabilla; Nieger, Martin; Bihlmeier, Angela; Shi, Min; Bräse, Stefan

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.

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Volltext §
DOI: 10.5445/IR/1000046412
Originalveröffentlichung
DOI: 10.1039/C4OB00234B
Scopus
Zitationen: 15
Web of Science
Zitationen: 15
Coverbild
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
urn:nbn:de:swb:90-464128
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 Web of Science
Scopus
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