General synthesis of α-acetoxy ethers from esters by DIBALH reduction and acetylation

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8317-8320

  Dahanukar, Vilas H ^a   Rychnovsky, Scott D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001268766     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961205m     Document Type: Article

References (24)

1. (a) Rychnovsky, S. D. J. Org. Chem. 1989, 54, 4982-4984.
2. (b) Rychnovsky, S. D.; Skalitzky, D. J. J. Org. Chem. 1992, 57, 4336-4339.
3. (a) Kiyooka, S.; Shirouchi, M.; Kaneko, Y. Tetrahedron Lett. 1993, 34, 1491-1494.
4. (b) Kiyooka, S.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 34, 5729-5732.
5. (c) Kiyooka, S.; Shirouchi, M. J. Org. Chem. 1992, 57, 1-2.
6. (a) Polt, R.; Peterson, M. A.; Deyoung, L. J. Org. Chem. 1982, 57, 5469-5480.
7. (b) Sames, D.; Liu, Y. Q.; Deyoung, L.; Polt, R. J. Org. Chem. 1995, 60, 2153-2159.
8. 3a
9. (a) Burke, S. D.; Deaton, D. N.; Olsen, R. J.; Armistead, D. M.; Blough, B. E. Tetrahedron Lett. 1987, 28, 3905-3906.
10. (b) Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N. J. Org. Chem. 1991, 56, 4370-4382.
11. (c) Ishihara, T.; Hayashi, H.; Yamananka, H. Tetrahedron Lett. 1993, 34, 5777-5780.
12. Shinokubo, H.; Oshima, K.; Utimoto, K. Chem. Lett. 1996, 461-462.
13. Prepared by Noyori ketalization of the corresponding aldehyde or ketone with trimethysilyl 3-[(trimethylsilyl)oxy]butyrate. (a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 27, 2945-2948. (c) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448-463.
14. Prepared by Noyori ketalization of the corresponding aldehyde or ketone with trimethysilyl 3-[(trimethylsilyl)oxy]butyrate. (a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 27, 2945-2948. (c) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448-463.
15. Prepared by Noyori ketalization of the corresponding aldehyde or ketone with trimethysilyl 3-[(trimethylsilyl)oxy]butyrate. (a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358. (b) Schreiber, S. L.; Reagan, J. Tetrahedron Lett. 1986, 27, 2945-2948. (c) Seebach, D.; Imwinkelried, R.; Stucky, G. Helv. Chim. Acta 1987, 70, 448-463.
16. Michael, A.; Weiner, N. J. Am. Chem. Soc. 1936, 58, 680-684.
17. Ziegler, E.; Junek, H.; Kroboth, H. Monatsch. Chem. 1976, 107, 317-324.
18. Schreiber, S. L. Chem. Scr. 1987, 27, 563.
19. Rychnovsky, S. D.; Skalitzky, D. J. Synlett 1995, 555-556.
20. Fotsch, C. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4141-4147.
21. Denmark's conditions were used in the coupling: Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458-6467.
22. Imwinkelried, R.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1985, 24, 756-757.
23. Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1993, 115, 9305-6.
24. 2 using oven dried glassware and standard syringe/septa techniques. DIBALH (1.0 M in eyclohexane), compounds 15 and 21 were purchased from Aldrich Chemical Co.