Designer chiral quaternary ammonium bifluorides as an efficient catalyst for asymmetric nitroaldol reaction of silyl nitronates with aromatic aldehydes

Journal of the American Chemical Society

Volumn 125, Issue 8, 2003, Pages 2054-2055

  Ooi, Takashi ^a   Doda, Kanae ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMMONIUM DERIVATIVE; FLUORIDE;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL MODIFICATION; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037466989     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029660p     Document Type: Article

References (35)

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5. For the asymmetric Michael addition of nitromethane, see: (a) Colonna, S.; Hiemstra, H.; Wynberg, H. Chem. Commun. 1978, 238. For the Mukaiyama-type reactions, see: (b) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (c) Shioiri, T.; Bohsako, A.; Ando, A. Heterocycles 1996, 42, 93. (d) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843. (e) Bluet, G.; Campagne, J.-M. J. Org. Chem. 2001, 66, 4293. For the trifluoromethylation of aldehydes, see: (f) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35. 3137. (g) Kuroki, Y.; Iseki, K. Tetrahedron Lett. 1999, 40, 8231.
6. For the asymmetric Michael addition of nitromethane, see: (a) Colonna, S.; Hiemstra, H.; Wynberg, H. Chem. Commun. 1978, 238. For the Mukaiyama-type reactions, see: (b) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (c) Shioiri, T.; Bohsako, A.; Ando, A. Heterocycles 1996, 42, 93. (d) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843. (e) Bluet, G.; Campagne, J.-M. J. Org. Chem. 2001, 66, 4293. For the trifluoromethylation of aldehydes, see: (f) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35. 3137. (g) Kuroki, Y.; Iseki, K. Tetrahedron Lett. 1999, 40, 8231.
7. For the asymmetric Michael addition of nitromethane, see: (a) Colonna, S.; Hiemstra, H.; Wynberg, H. Chem. Commun. 1978, 238. For the Mukaiyama-type reactions, see: (b) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (c) Shioiri, T.; Bohsako, A.; Ando, A. Heterocycles 1996, 42, 93. (d) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843. (e) Bluet, G.; Campagne, J.-M. J. Org. Chem. 2001, 66, 4293. For the trifluoromethylation of aldehydes, see: (f) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35. 3137. (g) Kuroki, Y.; Iseki, K. Tetrahedron Lett. 1999, 40, 8231.
8. For the asymmetric Michael addition of nitromethane, see: (a) Colonna, S.; Hiemstra, H.; Wynberg, H. Chem. Commun. 1978, 238. For the Mukaiyama-type reactions, see: (b) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (c) Shioiri, T.; Bohsako, A.; Ando, A. Heterocycles 1996, 42, 93. (d) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843. (e) Bluet, G.; Campagne, J.-M. J. Org. Chem. 2001, 66, 4293. For the trifluoromethylation of aldehydes, see: (f) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35. 3137. (g) Kuroki, Y.; Iseki, K. Tetrahedron Lett. 1999, 40, 8231.
9. For the asymmetric Michael addition of nitromethane, see: (a) Colonna, S.; Hiemstra, H.; Wynberg, H. Chem. Commun. 1978, 238. For the Mukaiyama-type reactions, see: (b) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (c) Shioiri, T.; Bohsako, A.; Ando, A. Heterocycles 1996, 42, 93. (d) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843. (e) Bluet, G.; Campagne, J.-M. J. Org. Chem. 2001, 66, 4293. For the trifluoromethylation of aldehydes, see: (f) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35. 3137. (g) Kuroki, Y.; Iseki, K. Tetrahedron Lett. 1999, 40, 8231.
10. For the asymmetric Michael addition of nitromethane, see: (a) Colonna, S.; Hiemstra, H.; Wynberg, H. Chem. Commun. 1978, 238. For the Mukaiyama-type reactions, see: (b) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (c) Shioiri, T.; Bohsako, A.; Ando, A. Heterocycles 1996, 42, 93. (d) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843. (e) Bluet, G.; Campagne, J.-M. J. Org. Chem. 2001, 66, 4293. For the trifluoromethylation of aldehydes, see: (f) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35. 3137. (g) Kuroki, Y.; Iseki, K. Tetrahedron Lett. 1999, 40, 8231.
11. For the use of in situ generated quaternary ammonium fluorides, see: (a) Carpino, L. A.; Sau, A. C. Chem. Commun. 1979, 514. (b) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931. (c) Ooi, T.; Doda, K,; Maruoka, K. Org. Lett. 2001, 3, 1273.
12. For the use of in situ generated quaternary ammonium fluorides, see: (a) Carpino, L. A.; Sau, A. C. Chem. Commun. 1979, 514. (b) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931. (c) Ooi, T.; Doda, K,; Maruoka, K. Org. Lett. 2001, 3, 1273.
13. For the use of in situ generated quaternary ammonium fluorides, see: (a) Carpino, L. A.; Sau, A. C. Chem. Commun. 1979, 514. (b) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931. (c) Ooi, T.; Doda, K,; Maruoka, K. Org. Lett. 2001, 3, 1273.
14. For our recent studies using this type of ammonium bromides as chiral phase-transfer catalysts, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
15. For our recent studies using this type of ammonium bromides as chiral phase-transfer catalysts, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
16. For our recent studies using this type of ammonium bromides as chiral phase-transfer catalysts, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
17. For our recent studies using this type of ammonium bromides as chiral phase-transfer catalysts, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
18. For our recent studies using this type of ammonium bromides as chiral phase-transfer catalysts, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
19. For our recent studies using this type of ammonium bromides as chiral phase-transfer catalysts, see: (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519. (b) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228. (c) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339. (d) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716. (e) Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551. (f) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
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34. - at δ -149.8 ppm. With the addition of 2a (2.4 equiv) at -78 °C, the sharp signal of trimethylsilyl fluoride appeared at δ -157.61 ppm, supporting generation of the corresponding chiral ammonium nitronate.
35. Attempted reaction of silyl nitronate 2a with heteroaromatic aldehyde, 2-furaldehyde, under similar conditions gave the corresponding nitroaldol 3 with moderate enantioselectivity [97% (anti/syn = 85:15), 77% ee (anti isomer)]. We also investigated aliphatic aldehydes in the nitroaldol reaction with 2a (at -78 °C for 0.5 h and -20 °C for 3 h), and the following results imply the present limitation of this method: 3-phenylpropanal [98% (anti/syn = 21:79), 46% ee (anti isomer), and 33% ee (syn isomer)]; cyclohexanecarboxaldehyde [87% (anti/syn = 43:57), 33% ee (anti isomer), and 20% ee (syn isomer)].