Chiral sulfoxides as neutral coordinate-organocatalysts in asymmetric allylation of N-acylhydrazones using allyltrichlorosilanes

Journal of the American Chemical Society

Volumn 125, Issue 22, 2003, Pages 6610-6611

  Kobayashi, Shũ ^a   Ogawa, Chikako ^a   Konishi, Hideyuki ^a   Sugiura, Masaharu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE DERIVATIVE; COORDINATION COMPOUND; HYDRAZONE DERIVATIVE; ORGANIC COMPOUND; SILANE DERIVATIVE; SULFOXIDE;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 0037871675     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035061m     Document Type: Article

References (37)

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2. For recent reviews on addition of allylmetals to imines and their analogues, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10. (c) Kobayashi, S.; Ishitani. H. Chem. Rev. 1999, 99, 1069. (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (e) Yamamoto, Y.; Asano, N. Chem. Rev. 1993, 93, 2207.
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7. For leading references on fluoride- or alkoxide-promoted allylation of imines with allylsilanes, see: (a) Sakurai, H. Synlett 1989, 1. (b) Wang, D.-K.; Zhou, Y.-G.; Tang, Y.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 1999, 64, 4233. (c) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901. (d) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. (e) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
8. For leading references on fluoride- or alkoxide-promoted allylation of imines with allylsilanes, see: (a) Sakurai, H. Synlett 1989, 1. (b) Wang, D.-K.; Zhou, Y.-G.; Tang, Y.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 1999, 64, 4233. (c) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901. (d) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. (e) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
9. For leading references on fluoride- or alkoxide-promoted allylation of imines with allylsilanes, see: (a) Sakurai, H. Synlett 1989, 1. (b) Wang, D.-K.; Zhou, Y.-G.; Tang, Y.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 1999, 64, 4233. (c) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901. (d) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. (e) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
10. For leading references on fluoride- or alkoxide-promoted allylation of imines with allylsilanes, see: (a) Sakurai, H. Synlett 1989, 1. (b) Wang, D.-K.; Zhou, Y.-G.; Tang, Y.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 1999, 64, 4233. (c) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901. (d) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614. (e) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
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17. A review on pentacoordinated silicon chemistry: Chuit, C. C.; Corriu, R. J.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. See also ref 2a.
18. Leading references for enantioselective allylations of aldehydes with allyltrichlorosilanes: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 (phosphoramides). (b) Denmark, S. E.; Coe, D. M.; Patt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161 (phosphoramides). (c) Nakajima, M.; Saito, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419 (pyridine N-oxides). (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977 (N-formamides). (e) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 124, 2477 (pyridine N-oxides).
19. Leading references for enantioselective allylations of aldehydes with allyltrichlorosilanes: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 (phosphoramides). (b) Denmark, S. E.; Coe, D. M.; Patt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161 (phosphoramides). (c) Nakajima, M.; Saito, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419 (pyridine N-oxides). (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977 (N-formamides). (e) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 124, 2477 (pyridine N-oxides).
20. Leading references for enantioselective allylations of aldehydes with allyltrichlorosilanes: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 (phosphoramides). (b) Denmark, S. E.; Coe, D. M.; Patt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161 (phosphoramides). (c) Nakajima, M.; Saito, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419 (pyridine N-oxides). (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977 (N-formamides). (e) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 124, 2477 (pyridine N-oxides).
21. Leading references for enantioselective allylations of aldehydes with allyltrichlorosilanes: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 (phosphoramides). (b) Denmark, S. E.; Coe, D. M.; Patt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161 (phosphoramides). (c) Nakajima, M.; Saito, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419 (pyridine N-oxides). (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977 (N-formamides). (e) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 124, 2477 (pyridine N-oxides).
22. Leading references for enantioselective allylations of aldehydes with allyltrichlorosilanes: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 (phosphoramides). (b) Denmark, S. E.; Coe, D. M.; Patt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161 (phosphoramides). (c) Nakajima, M.; Saito, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419 (pyridine N-oxides). (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977 (N-formamides). (e) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 124, 2477 (pyridine N-oxides).
23. Leading references for enantioselective allylations of imines using chiral catalysts, see: (a) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (b) Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168. (c) Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. (d) Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 1896. See also ref 2d.
24. Leading references for enantioselective allylations of imines using chiral catalysts, see: (a) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (b) Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168. (c) Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. (d) Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 1896. See also ref 2d.
25. Leading references for enantioselective allylations of imines using chiral catalysts, see: (a) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (b) Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168. (c) Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. (d) Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 1896. See also ref 2d.
26. Leading references for enantioselective allylations of imines using chiral catalysts, see: (a) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242. (b) Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168. (c) Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. (d) Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 1896. See also ref 2d.
27. Details are shown in the Supporting Information.
28. It was reported that DMSO was incompatible with allyltrichlorosilane (2) in a reaction with benzaldehyde (see ref 6b). Meanwhile. DMSO was employed as a solvent for aldol-type or Michael-type additions of ketene trimethylsilyl acetals or allylation of an aldehyde with allyltrimethylstan-nane where interaction of DMSO with these nucleophiles was suggested: (a) Génisson, Y.; Gorrichon, L. Tetrahedron Lett. 2000, 41, 4881. (b) Cokley, T. M.; Harvey, P. J.; Marshall, R. L.; McCluskey, A.; Young, D. J. J. Org. Chem. 1997, 62, 1961.
29. It was reported that DMSO was incompatible with allyltrichlorosilane (2) in a reaction with benzaldehyde (see ref 6b). Meanwhile. DMSO was employed as a solvent for aldol-type or Michael-type additions of ketene trimethylsilyl acetals or allylation of an aldehyde with allyltrimethylstan-nane where interaction of DMSO with these nucleophiles was suggested: (a) Génisson, Y.; Gorrichon, L. Tetrahedron Lett. 2000, 41, 4881. (b) Cokley, T. M.; Harvey, P. J.; Marshall, R. L.; McCluskey, A.; Young, D. J. J. Org. Chem. 1997, 62, 1961.
30. For recent reviews on chiral sulfoxides in organic synthesis, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Delouvrié, B.; Fensterbank, L.; Nájera, F.; Malacria, M. Eur. J. Org. Chem. 2002, 3507. (c) Solladié, G. Heteroat. Chem. 2002, 13, 443. For asymmetric catalysis using chiral sulfoxides as chiral ligands, see: (d) Hiroi, K. J. Synth. Org. Chem. Jpn. 2002, 60, 646 and references therein. (e) Priego, J.; García Mancheño, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. (f) Pezet, F.; Aït-Haddou, H.; Daran, J.-C.; Sasaki, I.; Balavoine, G. G. A. Chem. Commun. 2002, 510.
31. For recent reviews on chiral sulfoxides in organic synthesis, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Delouvrié, B.; Fensterbank, L.; Nájera, F.; Malacria, M. Eur. J. Org. Chem. 2002, 3507. (c) Solladié, G. Heteroat. Chem. 2002, 13, 443. For asymmetric catalysis using chiral sulfoxides as chiral ligands, see: (d) Hiroi, K. J. Synth. Org. Chem. Jpn. 2002, 60, 646 and references therein. (e) Priego, J.; García Mancheño, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. (f) Pezet, F.; Aït-Haddou, H.; Daran, J.-C.; Sasaki, I.; Balavoine, G. G. A. Chem. Commun. 2002, 510.
32. For recent reviews on chiral sulfoxides in organic synthesis, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Delouvrié, B.; Fensterbank, L.; Nájera, F.; Malacria, M. Eur. J. Org. Chem. 2002, 3507. (c) Solladié, G. Heteroat. Chem. 2002, 13, 443. For asymmetric catalysis using chiral sulfoxides as chiral ligands, see: (d) Hiroi, K. J. Synth. Org. Chem. Jpn. 2002, 60, 646 and references therein. (e) Priego, J.; García Mancheño, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. (f) Pezet, F.; Aït-Haddou, H.; Daran, J.-C.; Sasaki, I.; Balavoine, G. G. A. Chem. Commun. 2002, 510.
33. For recent reviews on chiral sulfoxides in organic synthesis, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Delouvrié, B.; Fensterbank, L.; Nájera, F.; Malacria, M. Eur. J. Org. Chem. 2002, 3507. (c) Solladié, G. Heteroat. Chem. 2002, 13, 443. For asymmetric catalysis using chiral sulfoxides as chiral ligands, see: (d) Hiroi, K. J. Synth. Org. Chem. Jpn. 2002, 60, 646 and references therein. (e) Priego, J.; García Mancheño, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. (f) Pezet, F.; Aït-Haddou, H.; Daran, J.-C.; Sasaki, I.; Balavoine, G. G. A. Chem. Commun. 2002, 510.
34. For recent reviews on chiral sulfoxides in organic synthesis, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Delouvrié, B.; Fensterbank, L.; Nájera, F.; Malacria, M. Eur. J. Org. Chem. 2002, 3507. (c) Solladié, G. Heteroat. Chem. 2002, 13, 443. For asymmetric catalysis using chiral sulfoxides as chiral ligands, see: (d) Hiroi, K. J. Synth. Org. Chem. Jpn. 2002, 60, 646 and references therein. (e) Priego, J.; García Mancheño, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. (f) Pezet, F.; Aït-Haddou, H.; Daran, J.-C.; Sasaki, I.; Balavoine, G. G. A. Chem. Commun. 2002, 510.
35. For recent reviews on chiral sulfoxides in organic synthesis, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Delouvrié, B.; Fensterbank, L.; Nájera, F.; Malacria, M. Eur. J. Org. Chem. 2002, 3507. (c) Solladié, G. Heteroat. Chem. 2002, 13, 443. For asymmetric catalysis using chiral sulfoxides as chiral ligands, see: (d) Hiroi, K. J. Synth. Org. Chem. Jpn. 2002, 60, 646 and references therein. (e) Priego, J.; García Mancheño, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. (f) Pezet, F.; Aït-Haddou, H.; Daran, J.-C.; Sasaki, I.; Balavoine, G. G. A. Chem. Commun. 2002, 510.
36. Allylations of N-acylhydrazones derived from cinnamaldehyde, 2-thiophenecarboxaldehyde, 3-pyridinecarboxaldehyde, and acetophenone resulted in low yields under the present reaction conditions.
37. Hydrazone of reacted with -4 sluggishly under the conditions.