Syntheses of Four Enantiomers of 2,3-Diendo- and 3-Endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic Acid and Their Saturated Analogues
Palkó, M., Hänninen, M. M., Sillanpää, R., & Fülöp, F. (2013). Syntheses of Four Enantiomers of 2,3-Diendo- and 3-Endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic Acid and Their Saturated Analogues. Molecules, 18(12), 15080-15093. https://doi.org/10.3390/molecules181215080
Julkaistu sarjassa
MoleculesPäivämäärä
2013Tekijänoikeudet
© 1996-2014 MDPI AG (Basel, Switzerland) unless otherwise stated. This is an article whose final and definitive form has been published by MDPI AG.
Abstract:
Ethyl 2,3-
diendo
-3-aminobicyclo[2.2.2]oct-
5-ene-2-carboxylate ((±)-
1
) was
resolved with
O
,
O
'-dibenzoyltartaric acid via diastere
omeric salt formation. The efficient
synthesis of the enantiomers of 2,3-
diendo
-3-aminobicyclo[2.2.2]oct-
5-ene-2-carboxylic
acid ((+)-
7
and (–)-
7
), 3-
endo
-aminobicyclo[2.2.2]oct-5-ene-2-
exo
-carboxylic acid ((+)-
5
and (–)-
5
),
cis
- and
trans
-3-aminobicyclo[2.2.2]octa
ne-2-carboxylic acid ((+)-
6
, (–)-
6
,
(+)-
8
and (–)-
8
) was achieved via isomerization,
hydrogenation and hydrolysis of the
corresponding esters (–)-
1
and (+)-
1
. The stereochemistry and relative configurations of the
synthesized compounds were determined by NMR spectroscopy (based on the
3
J
(H,H)
coupling constants) and
X-ray crystallography.
Julkaisija
M D P I AGISSN Hae Julkaisufoorumista
1420-3049Asiasanat
Alkuperäislähde
http://www.mdpi.com/1420-3049/18/12/15080Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/23768509
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