Acid-promoted rearrangement of α,β-epoxy acylates: Remarkable effects of an acyl group and a Lewis acid

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 1061-1064

  Kita, Yasuyuki ^a   Kitagaki, Shinji ^a   Yoshida, Yutaka ^a   Mihara, Sachiko ^a   Fang, Dai Fei ^a   Fujioka, Hiromichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL ALCOHOL; KETONE; SPIRO COMPOUND;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; PH; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562092     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02468-9     Document Type: Article

References (12)

1. 1. For examples where electron-donating hydroxy derivatives initiate cleavage of the oxirane ring at the α-position of the hydroxy function and successive migration, see: Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749-3762; Nagasawa, T.; Taya, K.; Kitamura, M. Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949-8950 and references cited therein. For rearrangement of epoxy alcohol derivative, see: Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944-5951 and references cited therein.
2. 1. For examples where electron-donating hydroxy derivatives initiate cleavage of the oxirane ring at the α-position of the hydroxy function and successive migration, see: Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749-3762; Nagasawa, T.; Taya, K.; Kitamura, M. Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949-8950 and references cited therein. For rearrangement of epoxy alcohol derivative, see: Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944-5951 and references cited therein.
3. 1. For examples where electron-donating hydroxy derivatives initiate cleavage of the oxirane ring at the α-position of the hydroxy function and successive migration, see: Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749-3762; Nagasawa, T.; Taya, K.; Kitamura, M. Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949-8950 and references cited therein. For rearrangement of epoxy alcohol derivative, see: Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944-5951 and references cited therein.
4. 2. For an example of epoxy acetates, see: Coxon, J. M.; Hartshorn, M. P.; Kirk, D. N. Tetrahedron 1964, 20, 2531-2545; 1964, 20, 2547-2552. In the cases, however, the yields of the rearranged products were very low and the regioselective cleavage of oxirane ring was not observed.
5. 2. For an example of epoxy acetates, see: Coxon, J. M.; Hartshorn, M. P.; Kirk, D. N. Tetrahedron 1964, 20, 2531-2545; 1964, 20, 2547-2552. In the cases, however, the yields of the rearranged products were very low and the regioselective cleavage of oxirane ring was not observed.
6. 3. Pittman, JR., C. U.; McManus, S. P.; Larsen, J. W. Chem. Rev. 1972, 72, 357-438.
7. 4. Fujioka, H.; Kitagaki, S.; Imai, R.; Kondo, M.; Okamoto, S.; Yoshida, Y.; Akai, S.; Kita, Y. Tetrahedron Lett. 1995, 36, 3219-3222.
8. 5. For preparation, see: Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 316-322.
9. 2, using the Mitsunobu reaction [Mitsunobu, O. Synthesis 1981, 1-28].
10. 2, 1N HCl was added to the mixture. The same procedure as stated above then gave the pure rearrangement product. Satisfactory spectroscopic data were obtained for all new compounds.
11. 8. (a) Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431-6432.
12. (b) Maruoka, K.; Ooi, T.; Nagahara, S.; Yamamoto, H. Tetrahedron 1991, 47, 6983-6998.