Highly stereoselective epoxidation of a 4-methyl-5- (triethylsilyl)oxyallyl alcohol system with m-chloroperoxybenzoic acid

Tetrahedron Letters

Volumn 39, Issue 25, 1998, Pages 4517-4520

  Maruyama, Kimiyuki ^a   Ueda, Masato ^a   Sasaki, Shinobu ^a   Iwata, Yasuhiro ^a   Miyazawa, Masahiro ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLOROPERBENZOIC ACID; 4 METHYL 5 (TRIETHYLSILYL)OXYALLYL ALCOHOL; ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; EPOXIDATION; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032543481     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00804-1     Document Type: Article

References (11)

1. 1 T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974; T. Katsuki and V. S. Martin, Org. React., 1996, 48, 1.
2. 1 T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974; T. Katsuki and V. S. Martin, Org. React., 1996, 48, 1.
3. 2 a) M. R. Johnson and Y. Kishi, Tetrahedron Lett., 1979, 4347;
4. b) M. Isobe, M. Kitamura, S. Mio, and T. Goto, ibid., 1982, 23, 221;
5. c) M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 1984, 49, 3517;
6. d) Y. Oikawa, T. Nishi, and O. Yonemitsu, J. Chem. Soc., Perkin Trans. I, 1985, 7.
7. 3 K. B. Jorgensen, H. Koshino, and T. Nakata., Heterocycles, 1998, 47, 679.
8. 4 M. Miyashita, M. Hoshino, and A. Yoshikoshi, J. Org. Chem., 1991, 56, 6483.
9. 5 M. Miyashita, K. Yoshihara, K. Kawamine, M. Hoshino, and H. Irie, Tetrahedron Lett., 1993, 34, 6285; M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama, and H. Irie, J. Chem. Soc. Chem. Commun., 1996, 1027.
10. 5 M. Miyashita, K. Yoshihara, K. Kawamine, M. Hoshino, and H. Irie, Tetrahedron Lett., 1993, 34, 6285; M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama, and H. Irie, J. Chem. Soc. Chem. Commun., 1996, 1027.
11. 6 We have found that some attempts to protect all the hydroxyl groups in the compounds having a polypropionate structure such as entries 6-9 by tert-butyldimethylsilyl groups were unsuccessful owing to steric interference, while their protection by triethylsilyl groups can be performed in excellent yields.