An efficient resolution of (±)-S-methyl-S-phenylsulfoximine with (±)-10-camphorsulfonic acid by the method of half-quantities

Tetrahedron Asymmetry

Volumn 8, Issue 6, 1997, Pages 909-912

  Brandt, Jochen ^a   Gais, Hans Joachim ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR DERIVATIVE; SULFOXIDE;

ARTICLE; CRYSTALLIZATION; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; SOLVATION; STEREOISOMERISM;

EID: 0030987106     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00046-3     Document Type: Article

References (17)

1. For reviews, see: (a) Johnson, C. R. In Comprehensive Organic Chemistry; Barton, D.; Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. l, p 223.
2. (b) Johnson, C. R. Aldrichimica Acta 1985, 18, 3.
3. (c) Barbachyn, M. R.; Johnson, C. R. In Asymmetric Synthesis; Morrison, J. D.; Scott, J. W., Eds.; Academic Press: New York, 1984; Vol. 4, p. 227.
4. (d) Pyne, S. G. Sulfur Reports 1992, 12, 57.
5. For most recent examples, see: (a) Bolm, C.; Kaufmann, D.; Zehnder, M.; Neuburger, M. Tetrahedron Lett. 1996, 37, 3985.
6. (b) Hainz, R.; Gais, H.-J.; Raabe, G. Tetrahedron: Asymmetry 1996, 7, 2505.
7. (c) Jackson, R. F. W.; Briggs, A. D.; Brown, P. A.; Clegg, W.; Frampton, C. J. Chem. Soc., Perkin Trans. I, 1996, 1673.
8. (d) Pyne, S. G.; Dong, Z. J. Org. Chem. 1996, 61, 5517.
9. Fusco, R.; Tericoni, F. Chim. Ind. (Milan) 1965, 47, 61.
10. Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418.
11. Shiner, C. S.; Berks, A. H. J. Org. Chem. 1988, 53, 5542.
12. Sulfoximines (+)-1 and (-)-l can also be prepared by imination of the corresponding optically sulfoxides (Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2458) which are accessible by catalytic asymmetric oxidation of methyl phenyl sulfide (Brunel, J.-M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086). Large scale synthesis of the sulfoximines by this route is hampered, however, by the necessity to use the hazardous reagent O-mesitylsulfonylhydroxylamine for the imination.
13. Sulfoximines (+)-1 and (-)-l can also be prepared by imination of the corresponding optically sulfoxides (Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2458) which are accessible by catalytic asymmetric oxidation of methyl phenyl sulfide (Brunel, J.-M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086). Large scale synthesis of the sulfoximines by this route is hampered, however, by the necessity to use the hazardous reagent O-mesitylsulfonylhydroxylamine for the imination.
14. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Krieger: Malabar, 1991 and references cited therein.
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16. Erdelmeier, I.; Gais, H.-J. J. Am. Chem. Soc. 1989, 111, 1125.
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