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Enantio- and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis-Decahydroquinolines.
Amat Tusón, Mercedes; Ghirardi, Elena; Navio, Laura; Griera Farres, Rosa; Llor Brunés, Núria; Molins i Grau, Elies; Bosch Cartes, Joan
Universitat de Barcelona
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.
Química orgànica
Alcaloides
Síntesi asimètrica
Lactames
Compostos heterocíclics
Organic chemistry
Alkaloids
Asymmetric synthesis
Lactams
Heterocyclic compounds
(c) Wiley-VCH, 2013
Article
info:eu-repo/semantics/acceptedVersion
Wiley-VCH
         

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