Diastereoselectivity in non-aldol aldol reactions: Silyl triflate-promoted Payne rearrangements

Tetrahedron Letters

Volumn 43, Issue 45, 2002, Pages 8169-8172

  Jung, Michael E ^a   van den Heuvel, Alexandra ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE; SILYL TRIFLATE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLIZATION; ISOMER;

EID: 0037020628     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01890-7     Document Type: Article

References (24)

1. Jung M.E., D'Amico D.C. J. Am. Chem. Soc. 115:1993;12208.
2. Jung M.E., D'Amico D.C. J. Am. Chem. Soc. 119:1997;12150.
3. Jung M.E., Karama U., Marquez R. J. Org. Chem. 64:1999;663.
4. Jung M.E., Marquez R. Tetrahedron Lett. 40:1999;3129.
5. Jung M.E., Lee W.S., Sun D. Org. Lett. 1:1999;307.
6. Jung M.E., Sun D. Tetrahedron Lett. 40:1999;8343.
7. Jung M.E., Marquez R. Org. Lett. 2:2000;1669.
8. Jung M.E., Lee C.P. Tetrahedron Lett. 41:2000;9719.
9. Jung M.E., Lee C.P. Org. Lett. 3:2001;333.
10. Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamune H., Sharpless K.B. J. Am. Chem. Soc. 109:1987;5765.
11. Rossiter B.E. Morrison J.D., Asymmetric Synthesis. 5:1985;193-243 Academic Press, New York.
12. Finn M.G., Sharpless K.B. Morrison J.D., Asymmetric Synthesis. 5:1985;247-308 Academic Press, New York.
13. The optical purity of the two diastereomers was determined to be about 80% by use of the Alexakis method: Alexakis A., Mutti S., Mangeney P. J. Org. Chem. 57:1992;1224.
14. The optical purity of the product 6 was identical to that of the starting epoxide indicating a stereospecific rearrangement.
15. The exact ratio of products 6 and 7 of the rearrangement of 5 is somewhat dependent on conditions and the silyl triflate used, with trimethylsilyl and triethylsilyl triflates (TMSOTf and TESOTf) giving about a 2:1 ratio and t-butyldimethylsilyl triflate (TBSOTf) affording about a 1:2 to 1:1 ratio, alkenes and other rearrangement products (vide infra) are formed in all cases.
16. Again the exact ratios of the eight products 9a-d and 10a-d vary depending on the exact conditions and the silyl triflate used. For example, the ratio of the four aldehydic products, 9a-d, is approximately 3:1.6:1.5:1 when the TES ether is treated with TES triflate and is 4.3:3.3:3:1 when the TBS ether is treated with TBS triflate (TBSOTf). The ketone ratios are similarly dependent of which combination of silyl ether and triflate are used.
17. Payne G.B. J. Org. Chem. 27:1962;3819.
18. See for example: (a) Wen, X.; Norling, H.; Hegedus, L. S. J. Org. Chem. 2000, 65, 2096; (b) Gillmore, A. T.; Roberts, S. M.; Hursthouse, M. B.; Abdul Malik, K. M. Tetrahedron Lett. 1998, 39, 3315; © Tius, M. A.; Reddy, N. K. Tetrahedron Lett. 1991, 32, 3605.
19. See for example: (a) Wen, X.; Norling, H.; Hegedus, L. S. J. Org. Chem. 2000, 65, 2096; (b) Gillmore, A. T.; Roberts, S. M.; Hursthouse, M. B.; Abdul Malik, K. M. Tetrahedron Lett. 1998, 39, 3315; © Tius, M. A.; Reddy, N. K. Tetrahedron Lett. 1991, 32, 3605.
20. See for example: (a) Wen, X.; Norling, H.; Hegedus, L. S. J. Org. Chem. 2000, 65, 2096; (b) Gillmore, A. T.; Roberts, S. M.; Hursthouse, M. B.; Abdul Malik, K. M. Tetrahedron Lett. 1998, 39, 3315; © Tius, M. A.; Reddy, N. K. Tetrahedron Lett. 1991, 32, 3605.
21. The structures of the two ketones were determined by comparison to authentic samples prepared by the Evans asymmetric aldol reaction, followed by formation of the Weinreb amide and addition of alkyl Grignard reagent.
22. Hoffmann R.W., Ditrich K., Froech S. Liebigs Ann. Chem. 1:1987;977.
23. Utaha M., Onoue S., Takeda A. Chem. Lett. 1987;971.
24. -1.