High Atom Efficiency in Sc(OTf)3-Catalyzed Allylation of Aldehydes with Tetraallyltin

Advanced Synthesis and Catalysis

Volumn 345, Issue 5, 2003, Pages 643-646

  Nagano, Yoshifumi ^a   Orita, Akihiro ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Acylation; Allylation; Lewis acids; Scandium; Stannanes

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; SCANDIUM; TETRAALLYLTIN; UNCLASSIFIED DRUG;

ALLYLATION; ATOM; CATALYSIS; REVIEW;

EID: 0038633743     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200202207     Document Type: Review

References (37)

1. a) B. M. Trost, Science 1991, 254, 1471;
2. b) R. A. Sheldon, Chem. Ind. (London) 1997, 12.
3. A. Yanagisawa, H. Inoue, M. Morodome, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10356.
4. a) T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, D. J. Young, J. Org. Chem. 1997, 62, 1961;
5. b) A. McCluskey, I. W. Muderawan Muntari, D. J. Young, J. Org. Chem. 2001, 66, 7811.
6. C. M. Gordon, A. McCluskey, Chem. Commun. 1999, 1431.
7. a) M. Yasuda, N. Kitahara, T. Fujibayashi, A. Baba, Chem. Lett. 1998, 743;
8. b) M. Yasuda, T. Fujibayashi, A. Baba, J. Org. Chem. 1998, 63, 6401.
9. I. Hachiya, S. Kobayashi, J. Org. Chem. 1993, 58, 6958.
10. S. Kobayashi, S. Nagayama, T. Busujima, Chem. Lett. 1997, 959.
11. For other relevant papers on the use of tetraallyltin in excess, see: a) D. N. Harpp, M. Gingras, J. Am. Chem. Soc. 1988, 110, 7737; b) S. Fukuzawa, K. Sato, T. Fujinami, S. Sakai, J. Chem. Soc. Chem. Commun. 1990, 939; c) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256; d) N. Asao, S. Kii, H. Hanawa, K. Maruoaka, Tetrahedron Lett. 1998, 39, 3729; e) H. C. Aspinall, N. Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9238; f) S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 7, 1061; g) R. Hamasaki, Y. Chounan, H. Horino, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 9883.
12. For other relevant papers on the use of tetraallyltin in excess, see: a) D. N. Harpp, M. Gingras, J. Am. Chem. Soc. 1988, 110, 7737; b) S. Fukuzawa, K. Sato, T. Fujinami, S. Sakai, J. Chem. Soc. Chem. Commun. 1990, 939; c) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256; d) N. Asao, S. Kii, H. Hanawa, K. Maruoaka, Tetrahedron Lett. 1998, 39, 3729; e) H. C. Aspinall, N. Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9238; f) S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 7, 1061; g) R. Hamasaki, Y. Chounan, H. Horino, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 9883.
13. For other relevant papers on the use of tetraallyltin in excess, see: a) D. N. Harpp, M. Gingras, J. Am. Chem. Soc. 1988, 110, 7737; b) S. Fukuzawa, K. Sato, T. Fujinami, S. Sakai, J. Chem. Soc. Chem. Commun. 1990, 939; c) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256; d) N. Asao, S. Kii, H. Hanawa, K. Maruoaka, Tetrahedron Lett. 1998, 39, 3729; e) H. C. Aspinall, N. Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9238; f) S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 7, 1061; g) R. Hamasaki, Y. Chounan, H. Horino, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 9883.
14. For other relevant papers on the use of tetraallyltin in excess, see: a) D. N. Harpp, M. Gingras, J. Am. Chem. Soc. 1988, 110, 7737; b) S. Fukuzawa, K. Sato, T. Fujinami, S. Sakai, J. Chem. Soc. Chem. Commun. 1990, 939; c) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256; d) N. Asao, S. Kii, H. Hanawa, K. Maruoaka, Tetrahedron Lett. 1998, 39, 3729; e) H. C. Aspinall, N. Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9238; f) S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 7, 1061; g) R. Hamasaki, Y. Chounan, H. Horino, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 9883.
15. For other relevant papers on the use of tetraallyltin in excess, see: a) D. N. Harpp, M. Gingras, J. Am. Chem. Soc. 1988, 110, 7737; b) S. Fukuzawa, K. Sato, T. Fujinami, S. Sakai, J. Chem. Soc. Chem. Commun. 1990, 939; c) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256; d) N. Asao, S. Kii, H. Hanawa, K. Maruoaka, Tetrahedron Lett. 1998, 39, 3729; e) H. C. Aspinall, N. Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9238; f) S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 7, 1061; g) R. Hamasaki, Y. Chounan, H. Horino, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 9883.
16. For other relevant papers on the use of tetraallyltin in excess, see: a) D. N. Harpp, M. Gingras, J. Am. Chem. Soc. 1988, 110, 7737; b) S. Fukuzawa, K. Sato, T. Fujinami, S. Sakai, J. Chem. Soc. Chem. Commun. 1990, 939; c) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256; d) N. Asao, S. Kii, H. Hanawa, K. Maruoaka, Tetrahedron Lett. 1998, 39, 3729; e) H. C. Aspinall, N. Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9238; f) S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 7, 1061; g) R. Hamasaki, Y. Chounan, H. Horino, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 9883.
17. For other relevant papers on the use of tetraallyltin in excess, see: a) D. N. Harpp, M. Gingras, J. Am. Chem. Soc. 1988, 110, 7737; b) S. Fukuzawa, K. Sato, T. Fujinami, S. Sakai, J. Chem. Soc. Chem. Commun. 1990, 939; c) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256; d) N. Asao, S. Kii, H. Hanawa, K. Maruoaka, Tetrahedron Lett. 1998, 39, 3729; e) H. C. Aspinall, N. Greeves, E. G. McIver, Tetrahedron Lett. 1998, 39, 9238; f) S. Casolari, D. D'Addario, E. Tagliavini, Org. Lett. 1999, 7, 1061; g) R. Hamasaki, Y. Chounan, H. Horino, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 9883.
18. a) J. Xiang, S. Toyoshima, A. Orita, J. Otera, Angew. Chem. Int. Ed. 2001, 40, 3670;
19. b) J. Xiang, A. Orita, J. Otera. Adv. Synth. Cat. 2002, 344, 84.
20. A. Orita, Y. Nagano, K. Nakazawa, J. Otera, Synlett 2000, 599.
21. V. K. Aggarwal, G. P. Vennall, Synthesis 1998, 1823.
22. a) K. Ishihara, S. Nakamura, M. Kaneeda, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 12854;
23. b) A. G. M. Barrett, D. C. Braddock, J. P. Henschke, E. R. Walker, J. Chem. Soc. Perkin Trans. 1 1999, 873;
24. K. Manabe, S. Kobayashi, Tetrahedron Lett. 1999, 40, 3773.
25. a) M. V. Deaton, M. A. Ciufolini, Tetrahedron Lett. 1993, 34, 2409;
26. b) M. A. Ciufolini, M. V. Deaton, S. Zhu, M. Chen, Tetrahedron 1997, 53, 16299;
27. H. C. Aspinall, J. S. Bissett, N. Greeves, D. Levin, Tetrahedron Lett. 2002, 43, 319.
28. 3.
29. A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, Y. Tomonaga, J. Org. Chem. 1990, 55, 2415.
30. K. Yamada, T. Tozawa, M. Nishida, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1997, 70, 2301.
31. T. Harada, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1993, 66, 882.
32. H. Yamataka, K. Nishikawa, T. Hanafusa, Chem. Lett. 1990, 1711.
33. X-H. Yi, J. X. Haberman, C-J. Li, Synth. Commun. 1998, 28, 2999.
34. M. Kira, K. Sato, H. Sakurai, J. Am. Chem. Soc. 1988, 110, 4599.
35. J. S. Yadav, B. V. Subba Reddy, G. S. Kiran Kumar Reddy, Tetrahedron Lett. 2000, 41, 2695.
36. G. A. Kraus, M. Silveira, S. J. Danko, J. Agric. Food Chem. 1984, 32, 1265.
37. C. Tanyeli, A. S. Demir, A. H. Arkin, I. M. Akhmedov, Enantiomer 1997, 2, 433.