Efficient two-step synthesis of salicylaldehydes via directed ortho-lithiation of in situ N-silylated O-aryl N-isopropylcarbamates

Synthesis

Volumn , Issue 10, 2006, Pages 1575-1577

  Kauch, Matthias ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Carbanions; Formylation; Lithiation; Phenols; Salicylaldehydes

Indexed keywords

AROMATIC COMPOUNDS; NEGATIVE IONS; PHENOLS; SYNTHESIS (CHEMICAL);

CARBANIONS; FORMYLATION; LITHIATION; SALICYLALDEHYDES;

ALDEHYDES;

CARBAMIC ACID DERIVATIVE; O ARYL N ISOPROPYLCARBAMIC ACID; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LITHIATION; SYNTHESIS;

EID: 33744481574     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926461     Document Type: Article

References (25)

1. Reviews: (a) Katsuki, T. Synlett 2003, 281.
2. (b) Katsuki, T. Chem. Soc. Rev. 2004, 33, 437.
3. Examples: (a) Wakamatsu, H.; Blechert, S. Angew. Chem. Int. Ed. 2002, 41, 794.
4. (b) Wakamatsu, H.; Blechert, S. Angew. Chem. Int. Ed. 2002, 41, 2403.
5. (c) Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502.
6. For a general review, see: Olah, G. A.; Ohannesian, L.; Arvanaghi, M. Chem. Rev. 1987, 87, 671.
7. (a) Casiraghi, G.; Casnati, G.; Cornia, M.; Pochini, A.; Puglia, G.; Sartori, G.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1 1978, 318.
8. (b) Wang, R. X.; You, X. Z.; Meng, Q. J.; Mintz, E. A.; Bu, X. R. Synth. Commun. 1994, 24, 1757.
9. Aldred, R.; Johnston, R.; Levin, D.; Neilan, J. J. Chem. Soc., Perkin Trans. 1 1994, 1823.
10. Hofsløkken, N. U.; Skattebøl, L. Acta Chem. Scand. 1999, 53, 258.
11. Reviews: (a) Snieckus, V. Chem. Rev. 1990, 90, 879.
12. (b) Clayden, J. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, 2004, 495.
13. (a) Kauch, M.; Snieckus, V.; Hoppe, D. J. Org. Chem. 2005, 70, 7149.
14. (b) Kauch, M.; Hoppe, D. Can. J. Chem. 2001, 79, 1736.
15. Casiraghi, G.; Casnati, G.; Puglia, G.; Sartori, G.; Terenghi, G. J. Chem. Soc., Perkin Trans. 1 1980, 1862.
16. Antonisse, M. M. G.; Snellink-Ruël, B. H. M.; Ion, A. C.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1999, 1211.
17. van Doorn, A. R.; Bos, M.; Harkema, S.; van Eerden, J.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1991, 56, 2371.
18. Christensen, H. Synth. Commun. 1975, 5, 65.
19. Aymes, D. J.; Paris, M. R. Bull. Soc. Chim. Fr. 1980, 175.
20. Mitani, M.; Furuyama, R.; Mohri, J.-i.; Saito, J.; Ishii, S.; Terao, H.; Nakano, T.; Tanaka, H.; Fujita, T. J. Am. Chem. Soc. 2003, 125, 4293.
21. García, O.; Nicolás, E.; Albericio, F. Tetrahedron Lett. 2003, 44, 4961.
22. Spagnolo, P.; Tiecco, M.; Tundo, A.; Martelli, G. J. Chem. Soc., Perkin Trans. 1 1972, 556.
23. Narasimhan, N. S.; Mali, R. S.; Barve, M. V. Synthesis 1979, 906.
24. The synthesis of 3-iodo- and 3-bromosalicylaldehyde by ipso-halodesilylation reactions of 4d is described in the accompanying paper: Kauch, M.; Hoppe, D. Synthesis 2006, xxx.
25. 8b or by reaction of 2-(trimethylsilyl)phenol with isopropyl isocyanate (96%).