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Enantio‐ and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis ‐Decahydroquinolines
Author(s) -
Amat Mercedes,
Ghirardi Elena,
Navío Laura,
Griera Rosa,
Llor Núria,
Molins Elies,
Bosch Joan
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302894
Subject(s) - enantiopure drug , diastereomer , stereocenter , desymmetrization , kinetic resolution , cyclohexanone , chemistry , stereochemistry , resolution (logic) , organic chemistry , enantioselective synthesis , catalysis , computer science , artificial intelligence
Up to four stereocenters with a well‐defined configuration are generated in a single synthetic step by the cyclocondensation of ( R )‐phenylglycinol or (1 S ,2 R )‐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.