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The Reactivity of Enantiopure ( S )‐6‐Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions
Author(s) -
Šafář Peter,
Marchalín Štefan,
Balónová Barbora,
Šoral Michal,
Moncol Ján,
Ghinet Alina,
Rigo Benoît,
Daïch Adam
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800908
Subject(s) - enantiopure drug , cationic polymerization , reactivity (psychology) , reagent , chemistry , residue (chemistry) , lactam , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , enantioselective synthesis
Enantiopure N ‐benzyl 6‐oxopipecolic acid, obtained from ( S )‐2‐aminoadipic acid, was evaluated under π‐cationic cyclization conditions. If the combination of SOCl 2 /AlCl 3 seems to be superior in terms of the reaction yields, use of PPA, (CF 3 CO) 2 O/BF 3 · Et 2 O, and Eaton's reagent is also very interesting since in addition to the expected keto‐lactam, reduced‐ and oxidized keto‐lactam, enamides and enamidones containing CF 3 CO– residue are isolated. Mechanisms leading to these products as well as the ones resulting from their acidic treatment were proposed and discussed with the help, in some cases, of univocal transformations and X‐ray analysis.