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Enantio- and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis-Decahydroquinolines.

By Mercedes Amat Tusón, Elena Ghirardi, Laura Navio, Rosa Griera Farres, Núria Llor Brunés, Elies Molins i Grau and Joan Bosch Cartes

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

Topics: Química orgànica, Alcaloides, Síntesi asimètrica, Lactames, Compostos heterocíclics, Organic chemistry, Alkaloids, Asymmetric synthesis, Lactams, Heterocyclic compounds
Publisher: Wiley-VCH
Year: 2016
DOI identifier: 10.1002/chem.201302894
OAI identifier: oai:diposit.ub.edu:2445/99269
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