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URN: urn:nbn:de:swb:90-464128

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.


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; LK 01
Erschienen in Organic & biomolecular chemistry
Band 12
Heft 20
Seiten 3265-3270
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