GaCl3-catalyzed skeletal rearrangement of α,α, α-trisubstituted aldehydes

Organic Letters

Volumn 7, Issue 2, 2005, Pages 331-334

  Oshita, Masayuki ^a   Okazaki, Takao ^b   Ohe, Kouichi ^b   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; GALLIUM CHLORIDE; KETONE;

ARTICLE; CATALYST; DENSITY FUNCTIONAL THEORY; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 13444309389     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047640h     Document Type: Article

References (25)

1. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 3.
2. For a review, see: Paquette, L. A.; Hofferberth, J. E. Org. React. 2003, 62, 477-567.
3. For recent papers, see: Ooi, T.; Saito, A.; Maruoka, K. J. Am. Chem. Soc. 2002, 125, 3220-3221. Suda, K.; Kikkawa, T.; Nakajima, S.; Takanami, T. J. Am. Chem. Soc. 2004, 126, 9554-9555.
4. For recent papers, see: Ooi, T.; Saito, A.; Maruoka, K. J. Am. Chem. Soc. 2002, 125, 3220-3221. Suda, K.; Kikkawa, T.; Nakajima, S.; Takanami, T. J. Am. Chem. Soc. 2004, 126, 9554-9555.
5. Danilov, S.; Venus-Danilova, E. Ber. Dtsch. Chem. Ges. 1926, 59, 377-387.
6. Hopff, H.; Nenizescu, C. D.; Isacescu, D. A.; Cantuiari, I. P. Chem. Ber. 1936, 69, 2244-2251.
7. Olah, G. A.; Mathew, T.; Marinez, E. R.; Esteves, P. M.; Etzkorn, M.; Rasul, G.; Prakash, G. K. S. J. Am. Chem. Soc. 2001, 125, 11556-11561.
8. Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 767-922. Olah, G. A.; Klumpp, D. A. Acc. Chem. Res. 2004, 37, 211-220.
9. Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 767-922. Olah, G. A.; Klumpp, D. A. Acc. Chem. Res. 2004, 37, 211-220.
10. Davies, H. M. L.; Dai, X. J. Am. Chem. Soc. 2004, 126, 2692-2693.
11. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294-10295. Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812-7813. Oshita, M.; Tobisu, M.; Yamashita, K.; Chatani, N. J. Am. Chem. Soc., in press.
12. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294-10295. Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812-7813. Oshita, M.; Tobisu, M.; Yamashita, K.; Chatani, N. J. Am. Chem. Soc., in press.
13. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294-10295. Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812-7813. Oshita, M.; Tobisu, M.; Yamashita, K.; Chatani, N. J. Am. Chem. Soc., in press.
14. Oshita, M.; Chatani, N. Org. Lett. 2004, 6, 4323-4325.
15. Olah, G. A.; Prakash, G. K. S.; Marinez, E. R. Angew. Chem., Int. Ed. 2000, 39, 2547-2548.
16. In the reaction of 10, the rearrangement product was isolated as a 4-tosylhydrazone because of the low boiling point of the product 11.
17. For papers on a double activation of aldehydes by bidentate organoaluminum Lewis acids, see: Ooi, T.; Takahashi, M.; Yamada, M.; Tayama, E.; Omoto, K.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 1150-1160.
18. For papers on diprotonated activation, see: Saito, S.; Sato, Y.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1994, 116, 2312-2317. Suzuki, T.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1997, 119, 6774-6780.
19. For papers on diprotonated activation, see: Saito, S.; Sato, Y.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1994, 116, 2312-2317. Suzuki, T.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1997, 119, 6774-6780.
20. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory, 2nd ed.; Wiley-VCH: New York, 2000.
21. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. Yonehara, F.; Kido, Y.; Sugimoto, H.; Morita, S.; Yamaguchi, M. J. Org. Chem. 2003, 68, 6752-6759. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991-4993. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601-603. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307-1314.
22. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. Yonehara, F.; Kido, Y.; Sugimoto, H.; Morita, S.; Yamaguchi, M. J. Org. Chem. 2003, 68, 6752-6759. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991-4993. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601-603. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307-1314.
23. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. Yonehara, F.; Kido, Y.; Sugimoto, H.; Morita, S.; Yamaguchi, M. J. Org. Chem. 2003, 68, 6752-6759. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991-4993. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601-603. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307-1314.
24. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. Yonehara, F.; Kido, Y.; Sugimoto, H.; Morita, S.; Yamaguchi, M. J. Org. Chem. 2003, 68, 6752-6759. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991-4993. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601-603. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307-1314.
25. Viswanathan, G. S.; Li, C.-J. Synlett 2002, 1553-1555. Yonehara, F.; Kido, Y.; Sugimoto, H.; Morita, S.; Yamaguchi, M. J. Org. Chem. 2003, 68, 6752-6759. Bez, G.; Zhao, C.-G. Org. Lett. 2003, 5, 4991-4993. Usugi, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601-603. Amemiya, R.; Nishimura, Y.; Yamaguchi, M. Synthesis 2004, 1307-1314.