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Title: Enantio- and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis-Decahydroquinolines.
Author: Amat Tusón, Mercedes
Ghirardi, Elena
Navio, Laura
Griera Farres, Rosa
Llor Brunés, Núria
Molins i Grau, Elies
Bosch Cartes, Joan
Keywords: Química orgànica
Síntesi asimètrica
Compostos heterocíclics
Organic chemistry
Asymmetric synthesis
Heterocyclic compounds
Issue Date: 18-Nov-2013
Publisher: Wiley-VCH
Abstract: Up to four stereocenters with a well-defined configuration are generated in a single synthetic step by the cyclocondensation of (R)-phenylglycinol or (1S,2R)-1-amino-2-indanol with stereoisomeric mixtures (racemates, meso forms, diastereoisomers) of cyclohexanone-based δ-keto-acid and δ-keto-diacid derivatives in enantio- and diastereoconvergent processes that involve dynamic kinetic resolution and/or desymmetrization of enantiotopic groups. A detailed analysis of the stereochemical outcome of this process is presented. This method provides easy access to enantiopure 8- and 6,8-substituted cis-decahydroquinolines, including alkaloids of the myrioxazine family.
Note: Versió postprint del document publicat a:
It is part of: Chemistry-A European Journal, 2013, vol. 19, num. 47, p. 16044-16049
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ISSN: 0947-6539
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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