1,8-Bis(allylstannyl)naphthalene derivatives as neutral allylation agents: Rate acceleration by chelation-induced lewis acidity

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 22, 1997, Pages 2507-2509

  Asao, Naoki ^a   Liu, Pingli ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Allylations; Chelates; Chemoselectivity; Lewis acidity; Tin

Indexed keywords

EID: 0031440077     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199725071     Document Type: Article

References (28)

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2. Review: a) Y. Yamamoto, Aldrichim. Ada 1987, 20, 45-49; b) Acc. Chem. Res. 1987, 20, 243-249; c) C. Hull, S. V. Mortlock, E. J. Thomas, Tetrahedron 1989, 45, 1007-1015; d) Y. Nishigaichi, A. Takuwa, Y. Naruta, K. Maruyama, ibid. 1993, 49, 7395-7426.
3. Review: a) Y. Yamamoto, Aldrichim. Ada 1987, 20, 45-49; b) Acc. Chem. Res. 1987, 20, 243-249; c) C. Hull, S. V. Mortlock, E. J. Thomas, Tetrahedron 1989, 45, 1007-1015; d) Y. Nishigaichi, A. Takuwa, Y. Naruta, K. Maruyama, ibid. 1993, 49, 7395-7426.
4. Review: a) Y. Yamamoto, Aldrichim. Ada 1987, 20, 45-49; b) Acc. Chem. Res. 1987, 20, 243-249; c) C. Hull, S. V. Mortlock, E. J. Thomas, Tetrahedron 1989, 45, 1007-1015; d) Y. Nishigaichi, A. Takuwa, Y. Naruta, K. Maruyama, ibid. 1993, 49, 7395-7426.
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8. Bronsted acid catalyzed allylation: a) S. E. Denmark, E. J. Weber, T. M. Wilson, T. M. Willson, Tetrahedron 1989, 45, 1053-1065; b) V. Gevorgyan, I. Kadota, Y. Yamamoto, Tetrahedron Lett. 1993, 34, 1313-1316.
9. 4NF-catalyzed allylation: Y. Yamamoto, S. Hatsuya, J. Yamada, J. Chem. Soc. Chem. Commun. 1987, 561-562.
10. High pressure induced allylation: a) Y. Yamamoto, K. Maruyama, K. Matsumoto, J. Chem. Soc. Chem. Commun. 1983, 489-490; b) N. S. Isaacs, R. L. Marshall, D. J. Young, Tetrahedron Lett. 1992, 33, 3023-3024; c) Y. Yamamoto, K. Saito, J. Chem. Soc. Chem. Commun. 1989, 1676-1678.
11. High pressure induced allylation: a) Y. Yamamoto, K. Maruyama, K. Matsumoto, J. Chem. Soc. Chem. Commun. 1983, 489-490; b) N. S. Isaacs, R. L. Marshall, D. J. Young, Tetrahedron Lett. 1992, 33, 3023-3024; c) Y. Yamamoto, K. Saito, J. Chem. Soc. Chem. Commun. 1989, 1676-1678.
12. High pressure induced allylation: a) Y. Yamamoto, K. Maruyama, K. Matsumoto, J. Chem. Soc. Chem. Commun. 1983, 489-490; b) N. S. Isaacs, R. L. Marshall, D. J. Young, Tetrahedron Lett. 1992, 33, 3023-3024; c) Y. Yamamoto, K. Saito, J. Chem. Soc. Chem. Commun. 1989, 1676-1678.
13. Photochemically induced allylation: A. Takuwa, H. Tagawa, H. Iwamoto, O. Soga, K. Maruyama, Chem. Lett. 1987, 1091-1094.
14. 1,8-Bis(metal)naphthalene derivatives as chelating Lewis acids: M. Reilly, T. Oh, Tetrahedron Lett. 1995, 36, 221-224, and references therein.
15. Behavior of chelating bis(halodiphenylstannyl) Lewis acids towards halide ions: D. Dakternieks, K. Jurkschat, H. Zhu, E. R. T. Tiekink, Organometallics 1995, 14, 2512-2521.
16. H. O. House, D. G. Koepsell, W. J. Campbell, J. Org. Chem. 1972, 37, 1003-1011.
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18. 4Sn as external standard): a) P. J. Smith, A. P. Tupciauskas, Annu. Rep. NMR Spectrosc. 1978, 8, 291-370; b) T. Kawakami, T. Sugimoto, I. Shibata, A. Baba, H. Matsuda, N. Sonoda, J. Org. Chem. 1995, 60, 2677-2682, and references therein.
19. M. Pereyre, J.-P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987, p. 200.
20. A. Hosomi, H. Iguchi, M. Endo, H. Sakurai, Chem. Lett. 1979, 977-980.
21. I. Pri-Bar, P. S. Pearlman, J. K. Stille, J. Org. Chem. 1983, 48, 4629-4634.
22. 2O (5/1) gave an allylation product in 82% yield; a yield of 62% was obtained in THF under similar reaction conditions.
23. The ratio of the allylation products from keto aldehyde 11 was determined by gas chromatography.
24. M. T. Reetz, B. Wenderoth, R. Peter, J. Chem. Soc. Chem. Commun. 1983, 406-408; see also M. T. Reetz, Organotitanium Reagents in Organic Synthesis, Springer, Berlin, 1986, p. 80.
25. M. T. Reetz, B. Wenderoth, R. Peter, J. Chem. Soc. Chem. Commun. 1983, 406-408; see also M. T. Reetz, Organotitanium Reagents in Organic Synthesis, Springer, Berlin, 1986, p. 80.
26. A. Yanagisawa, H. Inoue, M. Morodome, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10356-10357.
27. Use of excess prenyltributyltin (about 2-3 equiv) also gave none of the prenylation product.
28. The Lewis acidity of 1,8-bis(stannyl)naphthalene derivatives was also examined for the allylation of monostannane 2 with benzaldehyde in the presence of 1,8-bis(tributylstannyl)naphthalene as a bidentate Lewis acid under reaction conditions similar to those described for entry 4 of Table 1. Since the allylated product was obtained in higher yield (14%) than that in entry4, 1,8-bis(tributylstannyl)naphthalene seems to possess only weak Lewis acidity.