Aluminum bis(trifluoromethylsulfonyl)amides: New highly efficient and remarkably versatile catalysts for C-C bond formation reactions

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 178-181

  Marx, Andreas ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Aluminum; C C coupling; Lewis acids; Superacidic systems

Indexed keywords

ALUMINUM BIS(TRIFLUOROMETHYLSULFONYL)AMIDE; ALUMINUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0034598554     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000103)39:1<178::AID-ANIE178>3.0.CO;2-W     Document Type: Article

References (40)

1. Recent books: a) Lewis Acids Reagents (Ed.: H. Yamamoto), Oxford University Press, New York, 1999;
2. b) M. Santelli, J.-M. Pons, Lewis Acids and Selectivity in Organic Synthesis, CRC Press, New York, 1996.
3. c) Review: Y. Yamaguchi in Comprehensive Organic Synthesis, Vol 2 (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon, Oxford, 1991, p. 325.
4. a) P. J. Stang, M. Hanack, L. R. Subramanian, Synthesis 1982, 85;
5. b) P. J. Strang, M. R. White, Aldrichchimica Acta, 1983, 16, 15. For applications of various metal triflates in catalysis see ref. [1].
6. For general reviews for allylation of aldehydes, see a) J. A. Marshall, Chem. Rev. 1996, 96, 31;
7. b) Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207;
8. c) W. R. Roush in Comprehensive Organic Synthesis, Vol 2 (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon, Oxford, 1991.
9. IV complexes: D. R. Gauthier, E. M. Carreira, Angew. Chem. 1996, 108, 2521; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363.
10. IV complexes: D. R. Gauthier, E. M. Carreira, Angew. Chem. 1996, 108, 2521; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363.
11. IV complexes: D. R. Gauthier, E. M. Carreira, Angew. Chem. 1996, 108, 2521; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363.
12. A. Isshi, O. Kotera, T. Saeki, K. Mikami, Synlett 1997, 1145.
13. I. A. Koppel, R. W. Taft, F. Anvia, S.-Z. Zhu, L.-Q. Hu, K.-S. Sung, D. D. DesMarteau, L. M. Yagupolski, Y. L. Yagupolski, N. V. Ignatev, N. V. Kondratenko, A. Y. Volkonskii, V. M. Vlasov, R. Notario, P.-C. Maria, J. Am. Chem. Soc. 1994, 116, 3047.
14. a) H. C. Aspinall, A. F. Browning, N. Greeves, P. Ravenscroft, Tetrahedron Lett. 1994, 35, 4639;
15. b) H. C. Aspinall, N. Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9283.
16. B. Mathieu, L. Ghosez, Tetrahedron Lett. 1997, 38, 5497.
17. K. Mikami, O. Kotera, Y. Motoyama, H. Sakaguchi, M. Maruta, Synlett 1996, 171.
18. A. Bottoni, A. L. Costa, D. Di Tommaso, I. Rossi, E. Tagliavini, J. Am. Chem. Soc. 1997, 119, 12 131.
19. A side product formed in substantial amounts at 20 C was identified as the aldehyde cyclic trimer. See S. E. Denmark, N. G. Alstmtead, Tetrahedron 1992, 48, 5565.
20. a) Y. Nishigaichi, Y. Hanano, A. Takuwa, Chem. Lett. 1998, 33, and references therein;
21. b) A. Yanagisawa, Y. Nakatsuka, H. Nakashmia, H. Yamamoto, Synlett 1997, 933, and references therein;
22. b) Y. Nishigaichi, M. Fujimoto, A. Takuwa, J. Chem. Soc. Perkin Trans. I 1992, 2581;
23. d) D. Seyferth, J. Pornet, J. Org. Chem. 1980, 45, 1722.
24. a) Reviews: R. Mahrwald, Chem. Rev. 1999, 99, 1095; E. M. Vogel, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 1671; Angew. Chem. Int. Ed. 1999, 38, 1571;
25. a) Reviews: R. Mahrwald, Chem. Rev. 1999, 99, 1095; E. M. Vogel, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 1671; Angew. Chem. Int. Ed. 1999, 38, 1571;
26. a) Reviews: R. Mahrwald, Chem. Rev. 1999, 99, 1095; E. M. Vogel, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 1671; Angew. Chem. Int. Ed. 1999, 38, 1571;
27. b) T. K. Hollis, B. Bosnich, J. Am. Chem. Soc. 1995, 117, 4570, and references therein.
28. Cross-aldol reaction with activated trialkylsilylsulfonates: M. Oishi, S. Aratake, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 8271; by Reformatsky-type reactions: a) M. Maruoka, S. Hashimoto, Y. Kitagawa, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1977, 99, 7705;
29. Cross-aldol reaction with activated trialkylsilylsulfonates: M. Oishi, S. Aratake, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 8271; by Reformatsky-type reactions: a) M. Maruoka, S. Hashimoto, Y. Kitagawa, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1977, 99, 7705;
30. b) L. Weissjohan, H. Wild, Synthesis 1997, 512.
31. 3COTf: S. Kobayashi, M. Murakami, T. Mukaiyama, Chem. Lett. 1985, 953.
32. 3COTf: S. Kobayashi, M. Murakami, T. Mukaiyama, Chem. Lett. 1985, 953.
33. 3COTf: S. Kobayashi, M. Murakami, T. Mukaiyama, Chem. Lett. 1985, 953.
34. MAPH is not catalytically active under the reaction conditions employed. For chemoselective recognition by stoichiometric amounts of MAPH, see K. Maruoka, S. Saito, A. B. Conception, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1183; for use of other aluminum 2,6-diphenylphenoxides, see a) A. Marx, H. Yamamoto, Synlett 1999, 584;
35. MAPH is not catalytically active under the reaction conditions employed. For chemoselective recognition by stoichiometric amounts of MAPH, see K. Maruoka, S. Saito, A. B. Conception, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1183; for use of other aluminum 2,6-diphenylphenoxides, see a) A. Marx, H. Yamamoto, Synlett 1999, 584;
36. b) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1998, 110, 3213; Angew. Chem. Int. Ed. 1998, 37, 3039;
37. b) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1998, 110, 3213; Angew. Chem. Int. Ed. 1998, 37, 3039;
38. c) K. Maruoka, S. Saito, H. Yamamoto, Synlett 1994, 439.
39. 2NH (gas evolution) and was used without further purification.
40. K. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron 1997, 53, 3513.