1-[2-(Trimethylsilyl)ethoxy]ethyl (SEE): A novel hybrid hydroxy-protecting group between 1-(ethoxy)ethyl (EE) and 2-(trimethylsilyl)ethoxymethyl (SEM)

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3647-3650

  Wu, Junjun ^a   Shull, Brian K ^a   Koreeda, Masato ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; HYDROXYL GROUP;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029989133     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00663-6     Document Type: Article

References (22)

1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley: New York; 1991.
2. (b) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: New York; 1994.
3. (a) Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
4. (b) pp 77-83 in Ref 1a.
5. (c) pp 33-38 in Ref 1b.
6. (a) Lipshutz, B. H.; Pegram, J. J. Tetrahedron Lett. 1980, 21, 3343-3346.
7. (b) Lipshutz, B. H.; Pegram, J. J.; Morey, M. C. Ibid. 1981, 22, 4603-4606.
8. (c) pp 30-31 in Ref 1a.
9. (d) pp 80-82 in Ref. 1b.
10. (a) Lipshutz, B. H.; Miller, T. A. Tetrahedron Lett. 1989, 330, 7149-7152.
11. (b) Corey, E. J.; Yi, K. Y. Ibid. 1992, 33, 2289-2290. See also: Ref 1-3.
12. For silyl ether formation without the use of a base, see: (a) Clive, D. L. J.; Kellner, D. Tetrahedron Lett. 1991, 32, 7159-7160.
13. (b) Hardinger, S. A.; Wijaya, N. Ibid. 1993, 34, 3821-3824 and references cited therein.
14. Komarov, N. V.; Igonina, I.I. J. Gen. Chem. USSR (Engl. Transl.) 1967, 37, 1998-2001; Zh. Obshch. Khim. 1967, 37, 2108-2112. These authors prepared 4 in 75% yield by heating 2-(trimethylsilyl)ethyl 2′-chloroethyl ether at 350-400 °C in the presence of KOH powder.
15. Komarov, N. V.; Igonina, I.I. J. Gen. Chem. USSR (Engl. Transl.) 1967, 37, 1998-2001; Zh. Obshch. Khim. 1967, 37, 2108-2112. These authors prepared 4 in 75% yield by heating 2-(trimethylsilyl)ethyl 2′-chloroethyl ether at 350-400 °C in the presence of KOH powder.
16. Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772-3774.
17. See, e.g.: (a) Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286-5287.
18. (b) Stork, G.; Isobe, M. Ibid. 1975, 97, 1275-1276.
19. (c) Meyers, A. I.; Comins, D. L.; Roland, D. M.; Henning, R.; Shimizu, K. J. Am. Chem. Soc. 1979, 101, 7104-7105.
20. (d) Semmelhack, M. F.; Tomoda, S. Ibid. 1981, 103, 2427-2428.
21. (e) Fukuzawa, A.; Sato, H.; Masamune, T. Tetrahedron Lett. 1987, 28, 4303-4306.
22. 2O at room temperature (4 h).