Synthesis and structural characterization of enantiopure (2R,5R)-(+)-2,5-dimethylthiolane

Tetrahedron Asymmetry

Volumn 9, Issue 2, 1998, Pages 189-191

  Otten, Stephan ^a   Fröhlich, Roland ^a   Haufe, Günter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIMETHYLTHIOLANE; SULFONE; TETRAHYDROTHIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0344382102     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00621-6     Document Type: Article

References (16)

1. V. K. Aggarwal, M. Kalomiri, A. P. Thomas, Tetrahedron: Asymmetry 1994, 5, 723-730.
2. N. J. Archer, C. M. Rayner, D. Bell, D. Miller, Synlett 1994, 617-619.
3. (a) R. P. Short, R. M. Kennedy, S. Masamune, J. Org. Chem. 1989, 54, 1755-1756.
4. (b) M. J. Kim, I. S. Lee, Synlett 1993, 767-768.
5. (c) M. E. Zwaagstra, A. Meetsma, B. L. Feringa, Tetrahedron: Asymmetry 1993, 4, 2163-2172.
6. C. Wiesauer, C. Kratky, W. Weissensteiner, Tetrahedron: Asymmetry 1996, 7, 397-398.
7. S. Masamune, in Stereochemistry of Organic and Bioorganic Transformations, W. Bartmann, K. B. Sharpless, Eds.; VCH: Weinheim, 1987; pp. 49-72.
8. M. J. Kim, I. S. Lee, J. Org. Chem. 1993, 58, 6483-6485.
9. For a review see: J. K. Whitesell, Chem. Rev. 1989, 89, 1581-1590.
10. J. K. Lieser, Synth. Commun. 1983, 13, 765-767.
11. 3): δ 23.4 (q); 35.8 (t); 68.1 (d); MS (m/z): 118 (1); 100 (70); 85 (45); 83 (100); 45 (78); 41 (65).
12. Intensity data were collected on a CAD-4 diffractometer with ω/2θ scan mode, T=223 K, using monochromated CuKα radiation. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.
13. 2=0.101, GoF=1.175, based on anisotropic refinement of all non-hydrogen atoms. H atoms calculated and refined riding.
14. 12S (116.22), C 62.01, H 10.41, found C 61.97, H 10.47.
15. 2 (148.22), C 48.62, H 8.16, found C 48.41, H 8.05.
16. 2=0.120, GoF=1.083, based on anisotropic refinement of all non-hydrogen atoms, Flack parameter 0.09(3). H atoms calculated and refined riding.