Cyclopropanation reactions of enones with lithiated sulfoximines: Application to the asymmetric synthesis of chiral cyclopropanes

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2337-2343

  Pyne, Stephen G ^a   Dong, Zemin ^a   Skelton, Brian W ^b   White, Allan H ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0030989390     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962216i     Document Type: Article

References (23)

1. Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Chem. Soc., Chem. Commun. 1994, 751.
2. For previous studies on metalated allylic sulfoximines see: (a) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. (b) Pyne, S. G.; Boche, G. Tetrahedron 1993, 49, 8449. (c) Reggelin M.; Weinberger, H.; Gerlach, M.; Welcker, R. J. Am. Chem. Soc. 1996, 118, 4765 and references cited therein. (d) Hainz, R.; Gais, H. J.; Raabe, G. Tetrahedron: Asymmetry 1996, 7, 2505 and references cited therein.
3. For previous studies on metalated allylic sulfoximines see: (a) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. (b) Pyne, S. G.; Boche, G. Tetrahedron 1993, 49, 8449. (c) Reggelin M.; Weinberger, H.; Gerlach, M.; Welcker, R. J. Am. Chem. Soc. 1996, 118, 4765 and references cited therein. (d) Hainz, R.; Gais, H. J.; Raabe, G. Tetrahedron: Asymmetry 1996, 7, 2505 and references cited therein.
4. For previous studies on metalated allylic sulfoximines see: (a) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. (b) Pyne, S. G.; Boche, G. Tetrahedron 1993, 49, 8449. (c) Reggelin M.; Weinberger, H.; Gerlach, M.; Welcker, R. J. Am. Chem. Soc. 1996, 118, 4765 and references cited therein. (d) Hainz, R.; Gais, H. J.; Raabe, G. Tetrahedron: Asymmetry 1996, 7, 2505 and references cited therein.
5. For previous studies on metalated allylic sulfoximines see: (a) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. (b) Pyne, S. G.; Boche, G. Tetrahedron 1993, 49, 8449. (c) Reggelin M.; Weinberger, H.; Gerlach, M.; Welcker, R. J. Am. Chem. Soc. 1996, 118, 4765 and references cited therein. (d) Hainz, R.; Gais, H. J.; Raabe, G. Tetrahedron: Asymmetry 1996, 7, 2505 and references cited therein.
6. Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Chem. Soc., Chem. Commun. 1995, 445.
7. For some recent examples see: Yeh, S.-M.; Huang, L. H.; Luh, T.-Y. J. Org. Chem. 1996, 61, 3906. Doyle, M. P.; Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 13349. Mash, E. A.; Gregg, T. M.; Stahl, M. T. Walters, W. P. J. Org. Chem. 1996, 61, 2738 and references cited therein. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. Pique, C.; Fahndrich, B.; Pfaltz, A. Synlett 1995, 491. Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein.
8. For some recent examples see: Yeh, S.-M.; Huang, L. H.; Luh, T.-Y. J. Org. Chem. 1996, 61, 3906. Doyle, M. P.; Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 13349. Mash, E. A.; Gregg, T. M.; Stahl, M. T. Walters, W. P. J. Org. Chem. 1996, 61, 2738 and references cited therein. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. Pique, C.; Fahndrich, B.; Pfaltz, A. Synlett 1995, 491. Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein.
9. For some recent examples see: Yeh, S.-M.; Huang, L. H.; Luh, T.-Y. J. Org. Chem. 1996, 61, 3906. Doyle, M. P.; Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 13349. Mash, E. A.; Gregg, T. M.; Stahl, M. T. Walters, W. P. J. Org. Chem. 1996, 61, 2738 and references cited therein. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. Pique, C.; Fahndrich, B.; Pfaltz, A. Synlett 1995, 491. Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein.
10. For some recent examples see: Yeh, S.-M.; Huang, L. H.; Luh, T.-Y. J. Org. Chem. 1996, 61, 3906. Doyle, M. P.; Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 13349. Mash, E. A.; Gregg, T. M.; Stahl, M. T. Walters, W. P. J. Org. Chem. 1996, 61, 2738 and references cited therein. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. Pique, C.; Fahndrich, B.; Pfaltz, A. Synlett 1995, 491. Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein.
11. For some recent examples see: Yeh, S.-M.; Huang, L. H.; Luh, T.-Y. J. Org. Chem. 1996, 61, 3906. Doyle, M. P.; Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 13349. Mash, E. A.; Gregg, T. M.; Stahl, M. T. Walters, W. P. J. Org. Chem. 1996, 61, 2738 and references cited therein. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. Pique, C.; Fahndrich, B.; Pfaltz, A. Synlett 1995, 491. Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein.
12. For some recent examples see: Yeh, S.-M.; Huang, L. H.; Luh, T.-Y. J. Org. Chem. 1996, 61, 3906. Doyle, M. P.; Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 13349. Mash, E. A.; Gregg, T. M.; Stahl, M. T. Walters, W. P. J. Org. Chem. 1996, 61, 2738 and references cited therein. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393. Pique, C.; Fahndrich, B.; Pfaltz, A. Synlett 1995, 491. Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein.
13. Johnson, C. R.; Kirchhoff, R. A.; Reischer, R. J.; Katekar, G. F. J. Am. Chem. Soc. 1973, 95, 4287.
14. The stereochemistry of the minor diastereoisomers in Schemes 1, 5-7, and 10 and eq 1 have not been determined.
15. Upon deprotonation with BuLi, (S)-sulfoximines become (R)-lithiated sulfoximines.
16. Jackman, L. M.; Sternhell, S. In Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed.; Pergamon: Sydney, 1969; p 286.
17. Srikrishna, A.; Jagadeeswar Reddy, T. J. Org. Chem. 1996, 61, 6422.
18. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
19. Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Chem. Soc., Perkin Trans. 1 1994, 2607.
20. Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424.
21. Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2548.
22. Johnson, C. R.; Corkins, H. G. J. Org. Chem. 1978, 43, 4140.
23. The author has deposited the atomic coordinates for the structures 10 and 23a with the Cambridge Crystallography Data Centre. These coordinates can be obtained, on request, from the Director, Cambridge Crystallography Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.