Acid-promoted rearrangement of 2-aryl-2,3-epoxy acylates: Construction of chiral benzylic quaternary carbon centers

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2133-2136

  Kita, Yasuyuki ^a   Furukawa, Akihiro ^a   Futamura, Junko ^a   Higuchi, Kazuhiro ^a   Ueda, Koichiro ^a   Fujioka, Hiromichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 ARYL 2,3 EPOXY ACYLATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; CHIRALITY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034719737     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00092-7     Document Type: Article

References (14)

1. (a) Fujioka, H.; Kitagaki, S.; Imai, R.; Kondo, M.; Okamoto, S.; Yoshida, Y.; Akai, S.; Kita, Y. Tetrahedron Lett. 1995, 36, 3219-3222;
2. (b) Kita, Y.; Kitagaki, S.; Yoshida, Y.; Mihara, S.; Fang, D.-F.; Fujioka, H. Tetrahedron Lett. 1997, 38, 1061-1064;
3. (c) Kita, Y.; Kitagaki, S.; Yoshida, Y.; Mihara, S.; Fang, D.-F.; Kondo, M.; Okamoto, S.; Imai, R.; Akai, S.; Fujioka, H. J. Org. Chem. 1997, 62, 4991-4997;
4. (d) Kita, Y.; Yoshida, Y.; Kitagaki, S.; Mihara, S.; Fang, D.-F.; Furukawa, A.; Higuchi, K.; Fujioka, H. Tetrahedron 1999, 55, 4979-4998.
5. (a) Kita, Y.; Kitagaki, S.; Imai, R.; Okamoto, S.; Mihara, S.; Yoshida, Y.; Akai, S.; Fujioka, H. Tetrahedron Lett. 1996, 37, 1817-1820;
6. (b) Kita, Y.; Higuchi, K.; Yoshida, Y.; Iio, K.; Kitagaki, S.; Akai, S.; Fujioka, H. Angew. Chem. Int. Ed. 1999, 38, 683-686.
7. Rana, R. C.; Jana, V. J. Org. Chem. 1998, 63, 8212-8216.
8. The configuration of the quaternary carbon centers was determined by proposing a stereoselective rearrangement of the starting epoxy acylates.
9. Very recently, some related rearrangements have been reported in preliminary forms. They examined the rearrangement of the epoxy benzyl ether with a C3-aryl substituent and discussed the lifetime of the benzylic cation: Neef, G.; Baesler, S.; Depke, G.; Vierhufe, H. Tetrahedron Lett. 1999, 40, 7969-7973.
10. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7526. Absolute configuration of 7 was deduced by referring to the literature.
11. Enantiomeric excess of 7 was determined by HPLC analysis using the chiral column (Chiralcel OD).
12. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136-6137.
13. Mitsunobu, O.; Kimura, J.; Iizumi, K.; Yanagida, N. Bull. Chem. Soc. Jpn. 1976, 49, 510-513.
14. Enantiomeric excess of 9 was determined by HPLC analysis using the chiral column (Chiralcel OD).