Axially chiral 1,1''-binaphthyls with non-identical groups in 2,2'-positions. Synthesis of the enantiomerically pure 2-hydroxy-2'-thiol and substituted 2-amino-2'-thiols

Tetrahedron Asymmetry

Volumn 8, Issue 4, 1997, Pages 537-546

  Smrčina, Martin ^a   Vyskočil, Štěpán ^a,b   Polívková, Jana ^a   Poláková, Jana ^a   Sejbal, Jan ^a   Hanuš, Vladimír ^c   Polášek, Miroslav ^c   Verrier, Hugh ^d   Kočovský, Pavel ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

^c J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^d PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

THIOL DERIVATIVE;

ARTICLE; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031579476     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00539-3     Document Type: Article

References (57)

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39. 12. For another example of the configurational stability of the binaphthyl system under the conditions of Newman-Kwart rearrangement, see: Gladiali, S.; Dore, A.; Fabbri, D. Tetrahedron: Asymmetry 1994, 5, 1143.
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42. 15. Chromatography of 5 on a Chiralcel OD-H column indicated >97.4% ee for the crude product which, upon crystallization, gave pure material (>99% ee).
43. 16. Smrčina, M. Thesis, Charles University, Prague, 1992.
44. 10 However, there is no direct correlation of his results with those obtained by us for our experiments were carried out with the pure enantiomer.
45. 3b,c For details of the resolution procedure, see: Smrčina, M.; Vyskočil, Š.; Polívková, J.; Poláková, J.; Kočovský, P. Collect. Czech. Chem. Commun. 1996, 61, 1520.
46. 19. These are the optimized conditions; the reaction mixture contained a substantial amount of the starting material along with unidentified byproducts. However, prolonged heating led to gradual decomposition of the desired product, further lowering its yield. Higher temperature (260°C) had a similar effect.
47. 20. Guimanini, A. G.; Chiavari, G.; Musiani, M. M.; Rossi, P. Synthesis 1980, 743.
48. 21. (a) Moore, M. L. Org. React. 1949, 5, 301.
49. (b) Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
50. 2H at 150°C in autoclave was capricious (giving 30-65% yield and, in some batches, up to 40% of an unidentified byproduct), and led to a substantial racemization.
51. 23. The relatively high degree of racemization observed in this case can be tentatively attributed to the change of the geometry of the binaphthyl system due to cyclization.
52. 9 for 2 and 3 correspond, in fact, to racemates rather than to pure enantiomers.
53. 25. De Lucchi, O.; Fabbri, D.; Cossu, S.; Valle, G. J. Org. Chem. 1991, 56, 1888.
54. 4 in THF).
55. D -27.9 (c 1.0, EtOH) for the compound that can now be assigned the opposite configuration (see comments in Note 28): Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599.
56. 27 With our sample, the latter signal could be easily identified [at 0.59 (d, J=6.9 Hz) ppm], whereas the former doublet was essentially missing. Other methyl doublets of our sample corresponded to those reported by De Lucchi for one of the diastereoisomers (within ∼0.02 ppm), while those for the other could not be detected. These results indicate ≥98% ee for our sample. Moreover, the absolute configuration of 6 and the relative configuration of the De Lucchi's menthol-derived carbonates is thus unequivocally established.
57. D +50. By contrast, little changes were detected in THF over 24 h.