A simple and regioselective carbon-oxygen bond cleavage using Niobium(V)

Synlett

Volumn , Issue 6, 2004, Pages 1104-1106

  Arai, Shigeru ^a   Sudo, Yukinori ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Dealkylation; Friedel Crafts acylation; Niobium

Indexed keywords

ALKYL ARYL ETHER; BENZENE DERIVATIVE; CARBON; LEWIS ACID; NIOBIUM; OXYGEN; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL BOND; DIFFERENTIATION;

EID: 3142767415     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817766     Document Type: Article

References (12)

1. Roskamp, E. J.; Peredsen, S. F. J. Am. Chem. Soc. 1987, 109, 6551.
2. Kataoka, Y.; Miyai, J.; Tezuka, M.; Takai, K.; Ohshima, K.; Utimoto, K. Tetrahedron Lett. 1990, 31, 369.
3. Howarth, J.; Gillespie, K. Tetrahedron Lett. 1996, 37, 6011.
4. Andrade, C. K. Z.; Azevedo, N. R. Tetrahedron Lett. 2001, 42, 6473.
5. Andrade, C. K. Z.; Oliveira, G. R. Tetrahedron Lett. 2002, 43, 1935.
6. Guo, Q.; Miyaji, T.; Hara, R.; Shen, B.; Takahashi, T. Tetrahedron 2002, 58, 7327.
7. Ortiz, A.; Quintero, L.; Hernández, H.; Maldonado, S.; Mensoza, G.; Bernès, S. Tetrahedron Lett. 2003, 44, 1129.
8. Maeta, H.; Nagasawa, T.; Handa, Y.; Takei, T.; Osamura, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 899.
9. Yamamoto, M.; Nakazawa, M.; Kishikawa, K.; Kohmoto, S. Chem. Commun. 1996, 2353.
10. An example for the synthesis of mono-alky lethers of BINOL have been reported, see: Takahashi, M.; Ogasawara, K. Tetrahedron: Asymmetry 1997, 8, 3125.
11. 3 in C-O bond cleavage, unpublished results.
12. 4, and subsequent flash column chromatography (hexane:EtOAc = 8:1) gave the desired product 2a as a white amorphous (29.6 mg, 0.1 mmol, 100%).