Absolute configuration of Tröger bases: An X-ray diffraction and circular dichroism study

Tetrahedron Letters

Volumn 47, Issue 3, 2006, Pages 319-321

  Lenev, Denis A ^a   Lyssenko, Konstantin A ^b   Golovanov, Denis G ^b   Malyshev, Oleg R ^c   Levkin, Pavel A ^a   Kostyanovsky, Remir G ^a  

^a SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Absolute configuration; Circular dichroism; TD DFT Calculations; Tr ger bases; X ray diffraction analysis

Indexed keywords

METHYL GROUP;

ARTICLE; CALCULATION; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; ELECTRON; ENANTIOMER; SPECTROSCOPY; X RAY DIFFRACTION;

EID: 28844466692     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.019     Document Type: Article

References (24)

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19. + m/z 406.97518 (for C 17 H 17 Br 2 N 2 + calculated 406.97530), ee >95%. A single crystal was grown from EtOAc/n-hexane mixture under slow evaporation conditions. The details of the XRD analysis and absolute configuration determination of (5S,11S)-(-)-2 (excluding structure factors) were deposited at the Cambridge Crystallographic Data Centre as supplementary No. 253570. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
20. R.G. Kostyanovsky , V.R. Kostyanovsky , G.K. Kadorkina , and K.A. Lyssenko Mendeleev Commun. 2003 111 113
21. + m/z 251.15420 (for C 17 H 19 N 2 + calculated 251.15428), ee >95%.
22. Compound 2: Macherey-Nagel column Nucleodex-β-PM. Mixture of MeCN and water (1:1) was used as the mobile phase (1 ml/min flow rate). The retention times of the enantiomers are 10.3 and 11.5 min, the first eluted enantiomer was (5S,11S)-(-)-2. Compound 3: Daicel column Chiralcel OD. 0.5% isopropanol/hexane was used as the mobile phase (0.8 ml/min flow rate). The first eluted enantiomer was (5S,11S)-(-)-3, with a retention time of 9.7 min, (+)-3 elutes after 12.2 min. The resolutions were monitored by UV absorbance at 254 nm.
23. Computations were performed in the computing center of Cologne University (RRZK) using Gaussian 03, Revision B.04, Gaussian, Inc., Pittsburgh, PA, 2003.
24. R.G. Kostyanovsky, O.R. Malyshev, K.A. Lyssenko, Yu.A. Strelenko, G.K. Kadorkina, V.R. Kostyanovsky, O.G. Nabiev, and I.V. Fedyanin Mendeleev Commun. 2004 315