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2013-11-18

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/99269

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

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http://dx.doi.org/10.1002/chem.201302894

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.

Subject

Química orgànica, Alcaloides, Síntesi asimètrica, Lactames, Compostos heterocíclics

Subject (English)

Organic chemistry, Alkaloids, Asymmetric synthesis, Lactams, Heterocyclic compounds

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

Citation

AMAT TUSÓN, Mercedes, et al. Enantio- and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis-Decahydroquinolines. Chemistry-A European Journal. 2013. Vol. 19, num. 47, pags. 16044-16049. ISSN 0947-6539. [consulted: 17 of June of 2026]. Available at: https://hdl.handle.net/2445/99269

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