Stereoselective hydroxyalkylation of titanated allyl sulfoximines at the α- as well as the γ-position through variation of the titanation reagent

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2505-2508

  Hainz, Rüdiger ^a   Gais, Hans Joachim ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; REAGENT; TITANIUM;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030248570     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00318-7     Document Type: Article

References (24)

1. 1. Gais, H.-J.; Lenz, D.; Raabe, G. Tetrahedron Lett. 1995, 36, 7437.
2. 2. Gais, H.-J.; Müller, H.; Decker, J.; Mainz, R. Tetrahedron Lett, 1995, 36, 7433.
3. 3. For similar reactions of allyl sulfoximines bearing a chiral N-substituent, see: Reggelin, M.; Weinberger, H.; Gerlach. M.; Welcker, R. J. Am. Chem. Soc. 1996, 118, 4765 and earlier work cited therein.
4. 4. Gais, H.-J., Woo, C.-W.; Loo, R.; Raabe, G. Unpublished results.
5. 5. Gais, H.-J.; Bülow, G. Tetrahedron Lett. 1992, 33, 461.
6. 6. Gais, H.-J.; Bülow, G. Tetrahedron Lett. 1992, 33, 465.
7. 7. Erdelmeier, I.; Gais, H.-J. J. Am. Chem. Soc. 1989, 111, 1125.
8. 8. Reetz, M. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994, p 193.
9. 9. Full details of the crystal structure determination have been deposited at the Cambridge Crystallographic Data Centre, Lensfield Road, UK.
10. 10. Because of chemical arguments and similar relevant NMR data, the allyl sulfoximines E-3b, Z-3a and Z-3b were assigned the same absolute configuration as E-3a.
11. 11. Gais, H.-J.; Vollhardt, J.; Lindner, H. J.; Paulus, H. Angew. Chem. 1988, 100, 1598; Angew. Chem., Int. Ed. Engl. 1988, 27, 1540.
12. 11. Gais, H.-J.; Vollhardt, J.; Lindner, H. J.; Paulus, H. Angew. Chem. 1988, 100, 1598; Angew. Chem., Int. Ed. Engl. 1988, 27, 1540.
13. 12. Gais, H.-J.; Hess, T.; Raabe, G. Unpublished results.
14. 13.Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321.
15. 14. For a recent review on allyltitanium compounds, see: Hoppe, D. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; G. Thieme Verlag: Stuttgart, 1995, Vol. E21b, p 1551.
16. 15. For an enantio-divergent γ-hydroxyalkylation of a titanated allyl carbamate by variation of the titanation reagent, see: Krämer, T.; Hoppe, D. Tetrahedron Lett. 1987, 28, 5149.
17. 16. Harmata, M.; Claassen II, R. J. Tetrahedron Lett. 1991, 32, 6497.
18. 17.Pyne, S. G.; Boche, G. Tetrahedron 1993, 49, 8449.
19. 18. Satisfactory spectral and analytical data were obtained for all new compounds.
20. 19. Bund, J.; Gais, H.-J.; Erdelmeier, I. J. Am. Chem. Soc. 1991, 113, 1442.,
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23. 22.Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Chem. Soc., Chem. Commun. 1995, 445.
24. 23. Gais, H.-J.; Scommoda, M.; Lenz, D. Tetrahedron Lett. 1994, 35, 7361.