Palladium- and platinum-catalyzed addition of aldehydes and imines with allylstannanes. Chemoselective allylation of imines in the presence of aldehydes

Journal of the American Chemical Society

Volumn 118, Issue 28, 1996, Pages 6641-6647

  Nakamura, Hiroyuki ^a   Iwama, Hideki ^b   Yamamoto, Yoshinori ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029929193     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9608858     Document Type: Article

References (58)

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2. Recent reviews: (a) Y. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (c) Marshall, J. A. Chemtracts 1992, 5, 75. (d) Roush, W. R. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1-53. (e) Yamamoto, Y.; Shida, N. In Advances in Detailed Reaction Mechanisms; Coxon, J., Ed.; JAI Press: Greenwich, 1994; Vol. 3, pp 1-44.
3. Recent reviews: (a) Y. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (c) Marshall, J. A. Chemtracts 1992, 5, 75. (d) Roush, W. R. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1-53. (e) Yamamoto, Y.; Shida, N. In Advances in Detailed Reaction Mechanisms; Coxon, J., Ed.; JAI Press: Greenwich, 1994; Vol. 3, pp 1-44.
4. Recent reviews: (a) Y. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. (c) Marshall, J. A. Chemtracts 1992, 5, 75. (d) Roush, W. R. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1-53. (e) Yamamoto, Y.; Shida, N. In Advances in Detailed Reaction Mechanisms; Coxon, J., Ed.; JAI Press: Greenwich, 1994; Vol. 3, pp 1-44.
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23. Many of these reactions have been referred to as "Lewis acid catalyzed". However, this is not accurate. In general, an equivalent (or excess) amount of a Lewis acid has been used.
24. Lewis acid catalyzed allylation of aldehydes with allyltrimethylsilane has been reported, (a) Davis, A. P.; Jaspars, M. J. Chem. Soc., Chem. Commun. 1990, 1176. (b) Davis, A. P.; Jaspars, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 470. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. Brønsted acid catalyzed allylation of aldehydes with allyltributylstannane. (d) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. Lewis acid catalyzed asymmetric allylation of aldehydes with allylstannanes. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (g) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
25. Lewis acid catalyzed allylation of aldehydes with allyltrimethylsilane has been reported, (a) Davis, A. P.; Jaspars, M. J. Chem. Soc., Chem. Commun. 1990, 1176. (b) Davis, A. P.; Jaspars, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 470. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. Brønsted acid catalyzed allylation of aldehydes with allyltributylstannane. (d) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. Lewis acid catalyzed asymmetric allylation of aldehydes with allylstannanes. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (g) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
26. Lewis acid catalyzed allylation of aldehydes with allyltrimethylsilane has been reported, (a) Davis, A. P.; Jaspars, M. J. Chem. Soc., Chem. Commun. 1990, 1176. (b) Davis, A. P.; Jaspars, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 470. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. Brønsted acid catalyzed allylation of aldehydes with allyltributylstannane. (d) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. Lewis acid catalyzed asymmetric allylation of aldehydes with allylstannanes. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (g) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
27. Lewis acid catalyzed allylation of aldehydes with allyltrimethylsilane has been reported, (a) Davis, A. P.; Jaspars, M. J. Chem. Soc., Chem. Commun. 1990, 1176. (b) Davis, A. P.; Jaspars, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 470. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. Brønsted acid catalyzed allylation of aldehydes with allyltributylstannane. (d) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. Lewis acid catalyzed asymmetric allylation of aldehydes with allylstannanes. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (g) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
28. Lewis acid catalyzed allylation of aldehydes with allyltrimethylsilane has been reported, (a) Davis, A. P.; Jaspars, M. J. Chem. Soc., Chem. Commun. 1990, 1176. (b) Davis, A. P.; Jaspars, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 470. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. Brønsted acid catalyzed allylation of aldehydes with allyltributylstannane. (d) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. Lewis acid catalyzed asymmetric allylation of aldehydes with allylstannanes. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (g) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
29. Lewis acid catalyzed allylation of aldehydes with allyltrimethylsilane has been reported, (a) Davis, A. P.; Jaspars, M. J. Chem. Soc., Chem. Commun. 1990, 1176. (b) Davis, A. P.; Jaspars, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 470. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. Brønsted acid catalyzed allylation of aldehydes with allyltributylstannane. (d) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. Lewis acid catalyzed asymmetric allylation of aldehydes with allylstannanes. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (g) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
30. Lewis acid catalyzed allylation of aldehydes with allyltrimethylsilane has been reported, (a) Davis, A. P.; Jaspars, M. J. Chem. Soc., Chem. Commun. 1990, 1176. (b) Davis, A. P.; Jaspars, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 470. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. Brønsted acid catalyzed allylation of aldehydes with allyltributylstannane. (d) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313. Lewis acid catalyzed asymmetric allylation of aldehydes with allylstannanes. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (g) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
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33. 2.
34. 2.
35. 2.
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46. 3SnCl cannot be completely excluded.
47. Although π-allyl-π-methallyl complex is shown in eq 3, intervention of bis-π-allyl and bis-π-methallyl complexes cannot be ruled out completely.
48. The reactivity of crotylstanane 1b was typical. The reaction of 1b with benzaldehyde gave the adduct in only 37% yield after 4 days at room temperature, whereas the reaction with the corresponding imine afforded the allylated amine in essentially quantitative yield.
49. 2 gave better results.
50. Ciuforini, M. A.; Spencer, G. O. J. Org. Chem. 1989, 54, 4739. For transition metal catalyzed addition of pronucleophiles to the imines, see: Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161.
51. Ciuforini, M. A.; Spencer, G. O. J. Org. Chem. 1989, 54, 4739. For transition metal catalyzed addition of pronucleophiles to the imines, see: Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161.
52. 1 Quite recently, catalytic allylation of imines promoted by lanthanide inflates has been reported: Bellucci, C.; Cozzi, P.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. However, the chemical yields (30-70%) were generally low in the catalytic system.
53. 3a, 3b, 3h, and 3k: Chen, C.; Shen, Y.; Huang, Y. Tetrahedron Lett. 1988, 29, 1395. 3c: see ref 2a. 3d, 3l, and 3q: Nishigaichi, Y.; Nakao, N.; Takuwa, A. J. Chem. Soc., Perkin Trans. 1 1993, 11, 1203. 3e, 3j, 3m, 3n, 3o, and 3p: Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. 3f, 3i, and 3q: Shono, T.; Ishifune, M.; Kashimura, S. Chem. Lett. 1990, 449. 3g: see ref 2b.
54. 3a, 3b, 3h, and 3k: Chen, C.; Shen, Y.; Huang, Y. Tetrahedron Lett. 1988, 29, 1395. 3c: see ref 2a. 3d, 3l, and 3q: Nishigaichi, Y.; Nakao, N.; Takuwa, A. J. Chem. Soc., Perkin Trans. 1 1993, 11, 1203. 3e, 3j, 3m, 3n, 3o, and 3p: Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. 3f, 3i, and 3q: Shono, T.; Ishifune, M.; Kashimura, S. Chem. Lett. 1990, 449. 3g: see ref 2b.
55. 3a, 3b, 3h, and 3k: Chen, C.; Shen, Y.; Huang, Y. Tetrahedron Lett. 1988, 29, 1395. 3c: see ref 2a. 3d, 3l, and 3q: Nishigaichi, Y.; Nakao, N.; Takuwa, A. J. Chem. Soc., Perkin Trans. 1 1993, 11, 1203. 3e, 3j, 3m, 3n, 3o, and 3p: Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. 3f, 3i, and 3q: Shono, T.; Ishifune, M.; Kashimura, S. Chem. Lett. 1990, 449. 3g: see ref 2b.
56. 3a, 3b, 3h, and 3k: Chen, C.; Shen, Y.; Huang, Y. Tetrahedron Lett. 1988, 29, 1395. 3c: see ref 2a. 3d, 3l, and 3q: Nishigaichi, Y.; Nakao, N.; Takuwa, A. J. Chem. Soc., Perkin Trans. 1 1993, 11, 1203. 3e, 3j, 3m, 3n, 3o, and 3p: Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. 3f, 3i, and 3q: Shono, T.; Ishifune, M.; Kashimura, S. Chem. Lett. 1990, 449. 3g: see ref 2b.
57. 3a, 3b, 3h, and 3k: Chen, C.; Shen, Y.; Huang, Y. Tetrahedron Lett. 1988, 29, 1395. 3c: see ref 2a. 3d, 3l, and 3q: Nishigaichi, Y.; Nakao, N.; Takuwa, A. J. Chem. Soc., Perkin Trans. 1 1993, 11, 1203. 3e, 3j, 3m, 3n, 3o, and 3p: Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. 3f, 3i, and 3q: Shono, T.; Ishifune, M.; Kashimura, S. Chem. Lett. 1990, 449. 3g: see ref 2b.
58. 3a, 3b, 3h, and 3k: Chen, C.; Shen, Y.; Huang, Y. Tetrahedron Lett. 1988, 29, 1395. 3c: see ref 2a. 3d, 3l, and 3q: Nishigaichi, Y.; Nakao, N.; Takuwa, A. J. Chem. Soc., Perkin Trans. 1 1993, 11, 1203. 3e, 3j, 3m, 3n, 3o, and 3p: Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. 3f, 3i, and 3q: Shono, T.; Ishifune, M.; Kashimura, S. Chem. Lett. 1990, 449. 3g: see ref 2b.