Indium-mediated regio- and chemoselective synthesis of α-hydroxyalkyl allenic esters and gold-catalyzed cyclizations to ethyl 2-naphthoate derivatives

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3359-3362

  Park, Chansoo ^a   Lee, Phil Ho ^a  

^a Kangwon National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; ALKYNE; ALLENE; ESTER; GOLD; INDIUM; NAPHTHOL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALDEHYDES; ALKADIENES; ALKYLATION; ALKYNES; CATALYSIS; CYCLIZATION; ESTERS; GOLD; INDIUM; NAPHTHOLS;

EID: 49649099544     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801196g     Document Type: Article

References (33)

1. (a) Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621.
2. (b) Tsuboi, S.; Kuroda, H.; Takatsuka, S.; Fukawa, T.; Sakai, T.; Utaka, M. J. Org. Chem. 1983, 58, 5952.
3. (c) Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805.
4. (d) Deng, Y.; Jin, X; Ma, S. J. Org. Chem. 2007, 72, 5901.
5. (a) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. 1997, 36, 186.
6. (b) Krause, N.; Thorand, S. Inorg. Chim. Acta 1999, 296, 1.
7. (c) Krause, N.; Laux, M.; Hoffmann-Röder, A. Tetrahedron Lett. 2000, 41, 9613.
8. (d) Krause, N., ; Zelder, C. In The Chemistry of Dienes and Polyenes; Rappoport, Z., Ed.; Wiley: New York, 2000; Vol. 2, p 645.
9. Lin, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042.
10. (a) Hopf, H.; Bohm, I.; Kleinschroth, J. Org. Synth. 1982, 60, 41.
11. (b) Oehlsehlager, A. C.; Czyzewska, E. Tetrahedron Lett. 1983, 24, 5587.
12. (c) Brandsma, L.; Verkruijisse, H. In Preparative Polar Organometallic Chemistry I; Springer: Berlin, 1987; pp 61-64.
13. (d) Isaac, M. B.; Chan, T.-H. Chem. Commun. 1995, 1003.
14. (e) Masuyama, Y.; Ito, A.; Fukuzawa, M.; Terada, K.; Kurusu, Y. Chem. Commun. 1998, 2025.
15. (f) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149.
16. (g) Masuyama, Y.; Watabe, A.; Ito, A.; Kurusu, Y. Chem. Commun. 2000, 2009.
17. (h) Krause, N.; Hoffmann-Röder, A.; Cansius, J. Synthesis 2002, 1759.
18. (i) Hoffmann-Röder, A., ; Krause, N. In Modern Allene Chemistry; Krause, N., ; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 1,pp 51-92 and 493-592.
19. For allenylmagnesium halide and allenyllithium, see: (a) Babudri, F.; Florio, S. Synthesis 1986, 638.
20. (b) Shinokubo, H.; Miki, H.; Yokoo, T.; Oshima, K.; Utimoto, K. Tetrahedron 1995, 51, 11681.
21. (c) Weyershausen, B.; Nieger, M.; Dötz, K. H. Organometallics 1998, 17, 1602.
22. (d) Hoffmann-Röder, A., ; Krause, N. In Modern Allene Chemistry, Vol. 1, (Eds.; Krause, N., ; Hashmi, A. S. K., Eds.;Wiley-VCH: Weinheim, 2004; pp 497-499 and pp 509-510.
23. (a) Lee, P. H.; Sung, S.-Y.; Lee, K. Org. Lett. 2001, 3, 3201.
24. (b) Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901.
25. (c) Seomoon, D.; Lee, K.; Kim, H.; Lee, P. H. Chem.-Eur. J. 2007, 13, 5197.
26. MacInnes, I.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 1987, 1077.
27. (a) Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537.
28. (b) Hoffmann-Röder, A.; Krause, N. Org. Biomol. Chem. 2005, 3, 387.
29. (c) Gockel, B.; Krause, N. Org. Lett. 2006, 8, 4485.
30. (d) Hashmi, A. S. K.; Blanco, M. C.; Fischer, D.; Bats, J. W. Eur. J. Org. Chem. 2006, 1387.
31. (e) Hyland, C. J. T.; Hegedus, L. S. J. Org. Chem. 2006, 71, 8658.
32. (f) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
33. Skouta, R.; Li, C.-J. Can. J. Chem. 2008, 86, 616.