Asymmetric epoxy cyclohexenyl sulfones: Readily accessible progenitors of stereodefined six-carbon arrays

Organic Letters

Volumn 1, Issue 3, 1999, Pages 355-357

  Hentemann, Martin ^a   Fuchs, Philip L ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; SULFONE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM;

EPOXY COMPOUNDS; MOLECULAR CONFORMATION; STEREOISOMERISM; SULFONES;

EID: 0033549681     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990523f     Document Type: Article

References (33)

1. Syntheses via Vinyl Sulfones 81; Chiral Carbon Catalog 4.
2. Syntheses via Vinyl Sulfones 81; Chiral Carbon Catalog 4.
3. (a) Evans, D. A. Aldrichim. Acta 1982, 15, 23. Evans, D. A.; Ng, H. H.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127.
4. (a) Evans, D. A. Aldrichim. Acta 1982, 15, 23. Evans, D. A.; Ng, H. H.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127.
5. (b) Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993.
6. (c) Trost, B. M. Pure. Appl. Chem. 1996, 68, 779.
7. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
8. (e) Johnson, C. R. Acc. Chem. Res. 1998, 31, 333. Johnson, C. R.; Golebiowski, A.; Steensma, D. H. J. Am. Chem. Soc. 1992, 114, 9414.
9. (e) Johnson, C. R. Acc. Chem. Res. 1998, 31, 333. Johnson, C. R.; Golebiowski, A.; Steensma, D. H. J. Am. Chem. Soc. 1992, 114, 9414.
10. (f) Lautens, M.; Ren, Y.; Delanghe, P.; Chiu, P.; Ma, S.; Colucci, J. Can. J. Chem. 1995, 73, 1251 and references cited therein.
11. (a) Hentemann, M.; Fuchs, P. L. Tetrahedron Lett. 1999, 40, 2699-2702.
12. (b) Evarts, J. B., Jr.; Fuchs, P. L. Tetrahedron Lett. 1999, 40, 2703-2706.
13. Hentemann, M. F., Fuchs, P. L. Tetrahedron Lett. 1997, 38, 5615.
14. Bäckvall, J. E.; Juntunen, S. K.; Andell, O. S. Org. Synth. 1990, 68, 148. The 1,3-cyclohexadiene can be prepared very affordably from cyclohexene by dibromination and double elimination (Org. Synth. 1973, Coll. Vol. 5, 285). A more "environmentally friendly" approach to 1 has also been developed in four steps (∼60% overall) starting from cyclohexanone (Evarts, J., unpublished results).
15. Bäckvall, J. E.; Juntunen, S. K.; Andell, O. S. Org. Synth. 1990, 68, 148. The 1,3-cyclohexadiene can be prepared very affordably from cyclohexene by dibromination and double elimination (Org. Synth. 1973, Coll. Vol. 5, 285). A more "environmentally friendly" approach to 1 has also been developed in four steps (∼60% overall) starting from cyclohexanone (Evarts, J., unpublished results).
16. (a) Bäckvall, J.-E.; Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 1998, 98, 2291 and references cited therein.
17. By using vigorous mechanical stirring, 2 can be prepared using 1.5 mol % of the Jacobsen catalyst, and 6 mol % of the additive 4-phenylpropyl pyridine N-oxide and 1.5 equiv of commercial bleach after 15 min at 4°C. We have found that the ee % shows some decline with decreasing amounts of catalyst, with 2-4% being optimal for yield and >96% ee. Results of a systematic study will be presented in a later publication. ee % determined by HPLC using Daicel ChiralPak AD column.
18. Such directable reactions include cyclopropanation, dihydroxylation, aminohydroxylation, nucleophilic additions, etc. See: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
19. Absolute stereochemistry was determined by opening the epoxide to form the corresponding bromohydrin and obtaining crystallographic data.
20. (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
21. (b) Jain, N. F.; Takenaka, N.; Panek, J. S. J. Am. Chem. Soc. 1996, 118, 12475.
22. (c) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837.
23. (d) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Rieger, D. L. J. Am. Chem. Soc. 1995, 117, 9073.
24. Carbon, nitrogen, and halogen nucleophiles add in good yield in either a 1,2-or 1,4-sense (manuscript in preparation).
25. Paterson, I. Pure. Appl. Chem. 1992, 64, 1821.
26. Saddler, J. C.; Fuchs, P. L. J. Am. Chem. Soc. 1981, 103, 2112.
27. Miyashita, M.; Hoshino, M.; Yoshikoshi, A. J. Org. Chem. 1991, 56, 6483.
28. (a) Schank, K.; Werner, F. Liebigs Ann. Chem. 1979, 1977.
29. (b) Adam, W.; Hadjiarapoglou, L. Tetrahedron Lett. 1992, 33, 469.
30. (c) Claes, M. G.; Löfström, A. M.; Ericsson, L. B.; Juntunen, S. K.; Bäckvall, J. E. J. Org. Chem. 1995, 60, 3586.
31. (a) Hudlicky, T.; Luna, H.; Barbieri, G., Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
32. (b) Hudlicky, T.; Price, J. D., Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990, 112, 9439.
33. (c) Hudlicky, T.; Rouden, J.; Luna, H. J. Org. Chem. 1993, 58, 985.