Chiral Friedel-Crafts Alkylation of Aromatic Compounds Using Chiral Episulfonium Ions as Carbon Electrophiles

Synlett

Volumn 1996, Issue 5, 1996, Pages 465-467

  Toshimitsu, Akio ^a   Hirosawa, Chitaru ^a   Tamao, Kohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002948033     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5465     Document Type: Article

References (10)

1. (a) Toshimitsu, A.; Hirosawa, C.; Tanimoto, S. Tetrahedron Lett. 1991, 32, 4317.
2. (b) Toshimitsu, A.; Hirosawa, C.; Tamao, K. Tetrahedron 1994, 50, 8997.
3. (a) Toshimitsu, A.; Abe, H.; Hirosawa, C.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1992, 284.
4. (b) Toshimitsu, A.; Abe, H.; Hirosawa, C.; Tamao, K. J. Chem. Soc., Perkin Trans. 1 1994, 3465.
5. Toshimitsu, A.; Hirosawa, C.; Tanimoto, S. Chem. Lett. 1992, 239.
6. Electrophilic aromatic substitution by the intramolecular (non-chiral) episulfonium ion has been reported; (a) Edstrom, E. D.; Livinghouse, T. J. Am. Chem Soc. 1986, 108, 1334. (b) Kamimura, A.; Sasatani, H.; Hashimoto, T.; Ono, N. J. Org. Chem. 1989, 54, 4998.
7. Electrophilic aromatic substitution by the intramolecular (non-chiral) episulfonium ion has been reported; (a) Edstrom, E. D.; Livinghouse, T. J. Am. Chem Soc. 1986, 108, 1334. (b) Kamimura, A.; Sasatani, H.; Hashimoto, T.; Ono, N. J. Org. Chem. 1989, 54, 4998.
8. 3) (>99.7 %ee).
9. It has recently been reported that the anchimeric assistance by the 2,6-xylylthio or mesitylthio group is more effective than that by the phenylthio group: Hirosawa, C. Ph.D. Thesis, Kyoto University, 1994. Hashimoto, Y; Sato, Y.; Kudo, K.; Saigo, K. Tetrahedron Lett. 1993, 34, 7623.
10. It has recently been reported that the anchimeric assistance by the 2,6-xylylthio or mesitylthio group is more effective than that by the phenylthio group: Hirosawa, C. Ph.D. Thesis, Kyoto University, 1994. Hashimoto, Y; Sato, Y.; Kudo, K.; Saigo, K. Tetrahedron Lett. 1993, 34, 7623.