36415-87-9Relevant articles and documents
Enantiospecific synthesis and chiroptical properties of bicyclic enones
Orentas, Edvinas,Bagdziunas, Gintautas,Berg, Ulf,Zilinskas, Albinas,Butkus, Eugenijus
, p. 4251 - 4256 (2007)
The enantiospecific synthesis of several bicyclic enones starting from enantiomerically pure (+)-(1S,5S)-bicyclo[3.3.1]-nonane-2,6-dione (1) was accomplished. The target enones 7-9 were obtained in high yield and purity by using a catalytic amount of benzeneselenic anhydride. (+)-(1S,5R)-bicyclo[3.3.1] nonane-2,3,6-trione was obtained from diketone 1 by α-hydroxylation involving the use of iodine under basic conditions. The reaction included a ring closure/reopening sequence via oxatricyclo[4.3.1.03,8]decane-10-one. It was shown that the latter triketone exists in enone/enol form. Chiroptical properties of the enantiomerically pure compounds were studied, and the sign of the Cotton effect was related to the absolute configuration of the enones. The positive Cotton effect in the bisignate CD curve is accounted for by the nonplanarity of the chromophore in enones (1S,5R)-4 and (1S,5S)-8. The circular dichroism spectra provided evidence for interchromophoric interaction in dichromophoric bis(enone) 9. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis of enantiomerically pure (+)-(1S,2R,5S,6R)-endo,endo-2,6-diaminobicyclo[3.3.1]nonane
Butkus, Eugenius,Malinauskiene, Jule,Orentas, Edvinas,Zilinskas, Albinas
, p. 1595 - 1602 (2003)
Enantiospecific synthesis of enantiomerically pure (+)-(1S,2R, 5S,6R)-endo,endo-2,6-diaminobicyclo[3.3.1]nonane was accomplished via a reaction sequence including stereospecific synthesis of the corresponding dinitro compound and the subsequent reduction of the latter with LiAlH4. The title diamine wasalso obtained in a direct reduction of the corresponding dioxime with sodium in ethanol with high stereoselectivity.
EIN RASCHER ZUGANG ZU OPTISCH AKTIVEN ADAMANTAN-DERIVATEN
Hoffmann, Gerhard,Wiartalla, Rainer
, p. 3887 - 3888 (1982)
The stereospecific reduction using baker's yeast is an easy and efficient method for the resolution of bicyclononane-2,6-dione in a preparative scale from which optically active adamantane compounds are readily available.
Asymmetric cross-dimerization between methyl methacrylate and substituted alkene by Ru(0)-bicyclononadiene complex
Hiroi, Yuki,Komine, Nobuyuki,Komiya, Sanshiro,Hirano, Masafumi
supporting information, p. 2486 - 2489 (2013/07/05)
New Ru(0)-naphthalene complexes containing a bicyclononadiene ligand catalyze the linear cross-dimerization between methyl methacrylate and substituted alkenes by an oxidative coupling mechanism. The chiral (S,S)-2-methylbicyclo[3.3.1]nona-2,6-diene complex (S,S)-1b catalyzes asymmetric linear cross-dimerization between methyl methacrylate and 2,5-dihydrofuran to give the cross-dimer in 74% yield in 80% ee.
Baker's yeast for sweet dough enables large-scale synthesis of enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione
Wallentin, Carl Johan,Orentas, Edvinas,Butkus, Eugenijus,Waernmark, Kenneth
experimental part, p. 864 - 867 (2009/07/25)
An improved synthetic procedure of racemic bicyclo[3.3.1]nonane-2,6-dione has been developed. Employing Baker's yeast for sweet dough made it possible to kinetically resolve the racemic compound and to isolate enantiomerically pure (+)-bicyclo[3.3.1]nonane- 2,6-dione on a large scale. Furthermore, the developed procedure made it possible to produce (-)-bicyclo[3.3.1]nonane-2,6-dione with an enantiomeric excess of 75%. Georg Thieme Verlag Stuttgart.
