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Title: | Cyclocondensation reactions of racemic diastereomers of dimethyl-2-oxocyclohexanepropionic acids with (R)-phenylglycinol: access to both enantiomers of dimethyl cis-decahydroquinolines |
Author: | Calbó Zabala, Arnau Griera Farres, Rosa Bosch Cartes, Joan Amat Tusón, Mercedes |
Keywords: | Compostos heterocíclics Síntesi orgànica Heterocyclic compounds Organic synthesis |
Issue Date: | 14-Dec-2022 |
Publisher: | Royal Society of Chemistry |
Abstract: | Starting from racemic diastereomeric mixtures of dimethyl-2-oxocyclohexanepropionic acids (4-6) the synthesis of enantiopure 7,8-, 6,8-, and 5,8-dimethyl-substituted cis-decahydroquinolines (11, 13, and 15) and their enantiomers (ent-11, ent-13, and ent-15) is reported. The procedure involves a dynamic kinetic asymmetric transformation in the cyclocondensation of keto-acids 4-6 with (R)-phenylglycinol to give in each case two major oxazoloquinolone lactams (7a/7b, 8a/8b, 9a/9b), which differ in the absolute configuration of all the stereogenic centers except that of the chiral inductor. A subsequent two-step stereoselective removal of the phenylglycinol moiety with simultaneous reduction of the lactam carbonyl affords the enantiopure cis-decahydroquinolines in both enantiomeric series. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1039/D2QO01779B |
It is part of: | Organic Chemistry Frontiers, 2022, vol. 10, p. 724-729 |
URI: | http://hdl.handle.net/2445/194109 |
Related resource: | https://doi.org/10.1039/D2QO01779B |
ISSN: | 2052-4129 |
Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) |
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