Allylation of Aldehydes with Allyltin Compounds in Acidic Aqueous Media-A Catalytic Version

Synlett

Volumn 1997, Issue 11, 1997, Pages 1309-1311

  Yanagisawa, Akira ^a   Morodome, Miwa ^a   Nakashima, Hiroshi ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002552455     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1011     Document Type: Article

References (36)

1. Yanagisawa, A.: Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356.
2. 2O at 20 °C for 3 h to provide the homoallylic alcohol 4 in 8 % yield.
3. Recently, Young et al. found that tetraallyltin shows unusually high reactivity in methanol and reacts with aldehydes in high yield without any catalyst: (a) Cokley, T. M.; Marshall, R. L.; McCluskey, A.: Young, D. J. Tetrahedron Lett. 1996, 37, 1905. (b) Cokley, T. M.; Harvey, P. J.; Marshall, R. L.; McCluskey. A.; Young, D. J. J. Org. Chem. 1997, 62, 1961. For the reaction with acetals, see: (c) McCluskey, A.; Mayer, D. M.; Young, D. J. Tetrahedron Lett. 1997, 38, 5217. The rate acceleration of the reaction of tetraallyltin in methanol has also been reported by Baba et al.: (d) Yasuda, M.; Fujibayashi, T.; Shibata, I.; Baba, A. 70th Annual Meeting of the Chemical Society of Japan, Tokyo, March 28, 1996; 1J226.
4. Recently, Young et al. found that tetraallyltin shows unusually high reactivity in methanol and reacts with aldehydes in high yield without any catalyst: (a) Cokley, T. M.; Marshall, R. L.; McCluskey, A.: Young, D. J. Tetrahedron Lett. 1996, 37, 1905. (b) Cokley, T. M.; Harvey, P. J.; Marshall, R. L.; McCluskey. A.; Young, D. J. J. Org. Chem. 1997, 62, 1961. For the reaction with acetals, see: (c) McCluskey, A.; Mayer, D. M.; Young, D. J. Tetrahedron Lett. 1997, 38, 5217. The rate acceleration of the reaction of tetraallyltin in methanol has also been reported by Baba et al.: (d) Yasuda, M.; Fujibayashi, T.; Shibata, I.; Baba, A. 70th Annual Meeting of the Chemical Society of Japan, Tokyo, March 28, 1996; 1J226.
5. Recently, Young et al. found that tetraallyltin shows unusually high reactivity in methanol and reacts with aldehydes in high yield without any catalyst: (a) Cokley, T. M.; Marshall, R. L.; McCluskey, A.: Young, D. J. Tetrahedron Lett. 1996, 37, 1905. (b) Cokley, T. M.; Harvey, P. J.; Marshall, R. L.; McCluskey. A.; Young, D. J. J. Org. Chem. 1997, 62, 1961. For the reaction with acetals, see: (c) McCluskey, A.; Mayer, D. M.; Young, D. J. Tetrahedron Lett. 1997, 38, 5217. The rate acceleration of the reaction of tetraallyltin in methanol has also been reported by Baba et al.: (d) Yasuda, M.; Fujibayashi, T.; Shibata, I.; Baba, A. 70th Annual Meeting of the Chemical Society of Japan, Tokyo, March 28, 1996; 1J226.
6. Recently, Young et al. found that tetraallyltin shows unusually high reactivity in methanol and reacts with aldehydes in high yield without any catalyst: (a) Cokley, T. M.; Marshall, R. L.; McCluskey, A.: Young, D. J. Tetrahedron Lett. 1996, 37, 1905. (b) Cokley, T. M.; Harvey, P. J.; Marshall, R. L.; McCluskey. A.; Young, D. J. J. Org. Chem. 1997, 62, 1961. For the reaction with acetals, see: (c) McCluskey, A.; Mayer, D. M.; Young, D. J. Tetrahedron Lett. 1997, 38, 5217. The rate acceleration of the reaction of tetraallyltin in methanol has also been reported by Baba et al.: (d) Yasuda, M.; Fujibayashi, T.; Shibata, I.; Baba, A. 70th Annual Meeting of the Chemical Society of Japan, Tokyo, March 28, 1996; 1J226.
7. Most of the allylation reactions of carbonyl compounds in aqueous media reported are the Barbier-type reactions, see reviews: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (c) Li, C.-J. Tetrahedron 1996, 52, 5643.
8. Most of the allylation reactions of carbonyl compounds in aqueous media reported are the Barbier-type reactions, see reviews: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (c) Li, C.-J. Tetrahedron 1996, 52, 5643.
9. Most of the allylation reactions of carbonyl compounds in aqueous media reported are the Barbier-type reactions, see reviews: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (c) Li, C.-J. Tetrahedron 1996, 52, 5643.
10. 3: (e) Akiyama, T.: Iwai, J. Tetrahedron Lett. 1997, 38, 853.
11. 3: (e) Akiyama, T.: Iwai, J. Tetrahedron Lett. 1997, 38, 853.
12. 3: (e) Akiyama, T.: Iwai, J. Tetrahedron Lett. 1997, 38, 853.
13. 3: (e) Akiyama, T.: Iwai, J. Tetrahedron Lett. 1997, 38, 853.
14. 3: (e) Akiyama, T.: Iwai, J. Tetrahedron Lett. 1997, 38, 853.
15. (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; p 216.
16. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395.
17. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
18. Intramolecular allylic tributylstannane-aldehyde condensation reactions were accomplished by Brønsted acids: (a) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053. (b) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313.
19. Intramolecular allylic tributylstannane-aldehyde condensation reactions were accomplished by Brønsted acids: (a) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053. (b) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313.
20. Reactions of allyl- and allenyltin chlorides with carbonyl compounds in water or acid media were reported: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Gambaro, A. J. Organomet. Chem. 1985, 286, 9. (b) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (c) Furlani, D.; Marton, D.; Tagliavini, G.; Zordan, M. J. Organomet. Chem. 1988, 341, 345. (d) Marton, D.; Tagliavini, G.; Vanzan, N. J. Organomet. Chem. 1989, 376, 269.
21. Reactions of allyl- and allenyltin chlorides with carbonyl compounds in water or acid media were reported: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Gambaro, A. J. Organomet. Chem. 1985, 286, 9. (b) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (c) Furlani, D.; Marton, D.; Tagliavini, G.; Zordan, M. J. Organomet. Chem. 1988, 341, 345. (d) Marton, D.; Tagliavini, G.; Vanzan, N. J. Organomet. Chem. 1989, 376, 269.
22. Reactions of allyl- and allenyltin chlorides with carbonyl compounds in water or acid media were reported: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Gambaro, A. J. Organomet. Chem. 1985, 286, 9. (b) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (c) Furlani, D.; Marton, D.; Tagliavini, G.; Zordan, M. J. Organomet. Chem. 1988, 341, 345. (d) Marton, D.; Tagliavini, G.; Vanzan, N. J. Organomet. Chem. 1989, 376, 269.
23. Reactions of allyl- and allenyltin chlorides with carbonyl compounds in water or acid media were reported: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Gambaro, A. J. Organomet. Chem. 1985, 286, 9. (b) Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 297, 149. (c) Furlani, D.; Marton, D.; Tagliavini, G.; Zordan, M. J. Organomet. Chem. 1988, 341, 345. (d) Marton, D.; Tagliavini, G.; Vanzan, N. J. Organomet. Chem. 1989, 376, 269.
24. Preparation: (a) Jones, W. J.; Davies, W. C.; Bowden, S. T.; Edwards, C.; Davis, V. E.; Thomas, L. H. J. Chem. Soc. 1947, 1446. (b) Dang, H.-S.; Davies, A. G. J. Organomet. Chem. 1992, 430, 287. (c) Carofiglio, T.; Marton, D.; Tagliavini, G. Organometallics 1992, 11, 2961.
25. Preparation: (a) Jones, W. J.; Davies, W. C.; Bowden, S. T.; Edwards, C.; Davis, V. E.; Thomas, L. H. J. Chem. Soc. 1947, 1446. (b) Dang, H.-S.; Davies, A. G. J. Organomet. Chem. 1992, 430, 287. (c) Carofiglio, T.; Marton, D.; Tagliavini, G. Organometallics 1992, 11, 2961.
26. Preparation: (a) Jones, W. J.; Davies, W. C.; Bowden, S. T.; Edwards, C.; Davis, V. E.; Thomas, L. H. J. Chem. Soc. 1947, 1446. (b) Dang, H.-S.; Davies, A. G. J. Organomet. Chem. 1992, 430, 287. (c) Carofiglio, T.; Marton, D.; Tagliavini, G. Organometallics 1992, 11, 2961.
27. 2), 4.75 (dt, 1 H, J = 6.9, 2.5 Hz, CH), 5.14-5.20 (m, 2 H, 2 vinyls), 5.82 (m, 1 H, vinyl), 7.25-7.37 (m, 5 H, aromatic).
28. Concerning the reactivity of allyltin chlorides, see: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Ganis, P. J. Organomet. Chem. 1987, 321, 199. See also ref.8. (b) Marshall, R. L.; Young, D. J. Tetrahedron Lett. 1992, 33, 2369. (c) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 1369. (d) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 2221. (e) Fouquet, E.; Gabriel, A.; Maillard, B.; Pereyre, M. Bull. Soc. Chim. Fr. 1995, 132, 590.
29. Concerning the reactivity of allyltin chlorides, see: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Ganis, P. J. Organomet. Chem. 1987, 321, 199. See also ref.8. (b) Marshall, R. L.; Young, D. J. Tetrahedron Lett. 1992, 33, 2369. (c) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 1369. (d) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 2221. (e) Fouquet, E.; Gabriel, A.; Maillard, B.; Pereyre, M. Bull. Soc. Chim. Fr. 1995, 132, 590.
30. Concerning the reactivity of allyltin chlorides, see: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Ganis, P. J. Organomet. Chem. 1987, 321, 199. See also ref.8. (b) Marshall, R. L.; Young, D. J. Tetrahedron Lett. 1992, 33, 2369. (c) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 1369. (d) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 2221. (e) Fouquet, E.; Gabriel, A.; Maillard, B.; Pereyre, M. Bull. Soc. Chim. Fr. 1995, 132, 590.
31. Concerning the reactivity of allyltin chlorides, see: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Ganis, P. J. Organomet. Chem. 1987, 321, 199. See also ref.8. (b) Marshall, R. L.; Young, D. J. Tetrahedron Lett. 1992, 33, 2369. (c) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 1369. (d) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 2221. (e) Fouquet, E.; Gabriel, A.; Maillard, B.; Pereyre, M. Bull. Soc. Chim. Fr. 1995, 132, 590.
32. Concerning the reactivity of allyltin chlorides, see: (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Ganis, P. J. Organomet. Chem. 1987, 321, 199. See also ref.8. (b) Marshall, R. L.; Young, D. J. Tetrahedron Lett. 1992, 33, 2369. (c) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 1369. (d) Miyake, H.; Yamamura, K. Chem. Lett. 1992, 2221. (e) Fouquet, E.; Gabriel, A.; Maillard, B.; Pereyre, M. Bull. Soc. Chim. Fr. 1995, 132, 590.
33. D -33.2° (c 1.0, benzene). (a) Otera, J.; Kawasaki, Y.; Mizuno, H.; Shimizu, Y. Chem. Lett. 1983, 1529. (b) Otera, J.; Yoshinaga, Y.; Yamaji, T.; Yoshioka, T.; Kawasaki, Y. Organometallics 1985, 4, 1213.
34. D -33.2° (c 1.0, benzene). (a) Otera, J.; Kawasaki, Y.; Mizuno, H.; Shimizu, Y. Chem. Lett. 1983, 1529. (b) Otera, J.; Yoshinaga, Y.; Yamaji, T.; Yoshioka, T.; Kawasaki, Y. Organometallics 1985, 4, 1213.
35. 1H NMR analysis of the MTPA ester.
36. 2O). The enantioselectivity was determined by HPLC analysis (Chiralcel OD, Daicel Chemical Industries, Ltd.).