Stereoselective Mannich-type reaction of chiral aldimines with 2-silyloxybutadienes by using trifluoromethanesulfonic acid

Tetrahedron Letters

Volumn 44, Issue 29, 2003, Pages 5441-5444

  Ishimaru, Kaori ^a   Kojima, Takakazu ^a  

^a NATIONAL DEFENSE ACADEMY   (Japan)

Author keywords

Dienes; Imines; Mannich reactions; Stereocontrol

Indexed keywords

ALKADIENE; IMINE; LEWIS ACID; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0038200900     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01314-5     Document Type: Article

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8. Recent examples of Mannich-type reactions, see: (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143; (b) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463; (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983; (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640; (e) Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652; (f) Takahashi, H.; Kashiwa, N.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2002, 43, 2935; (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284; (h) Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338; (i) Loh, T.-P.; Chen, S.-L. Org. Lett. 2002, 4, 3647; (j) Akiyama, T.; Ito, J.; Fuchibe, K. Synlett 2002, 1269; (k) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
9. Recent examples of Mannich-type reactions, see: (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143; (b) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463; (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983; (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640; (e) Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652; (f) Takahashi, H.; Kashiwa, N.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2002, 43, 2935; (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284; (h) Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338; (i) Loh, T.-P.; Chen, S.-L. Org. Lett. 2002, 4, 3647; (j) Akiyama, T.; Ito, J.; Fuchibe, K. Synlett 2002, 1269; (k) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
10. Recent examples of Mannich-type reactions, see: (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143; (b) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463; (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983; (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640; (e) Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652; (f) Takahashi, H.; Kashiwa, N.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2002, 43, 2935; (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284; (h) Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338; (i) Loh, T.-P.; Chen, S.-L. Org. Lett. 2002, 4, 3647; (j) Akiyama, T.; Ito, J.; Fuchibe, K. Synlett 2002, 1269; (k) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
11. Recent examples of Mannich-type reactions, see: (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143; (b) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463; (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983; (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640; (e) Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652; (f) Takahashi, H.; Kashiwa, N.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2002, 43, 2935; (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284; (h) Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338; (i) Loh, T.-P.; Chen, S.-L. Org. Lett. 2002, 4, 3647; (j) Akiyama, T.; Ito, J.; Fuchibe, K. Synlett 2002, 1269; (k) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
12. Recent examples of Mannich-type reactions, see: (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143; (b) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463; (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983; (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640; (e) Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652; (f) Takahashi, H.; Kashiwa, N.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2002, 43, 2935; (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284; (h) Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338; (i) Loh, T.-P.; Chen, S.-L. Org. Lett. 2002, 4, 3647; (j) Akiyama, T.; Ito, J.; Fuchibe, K. Synlett 2002, 1269; (k) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
13. Recent examples of Mannich-type reactions, see: (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143; (b) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463; (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983; (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640; (e) Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652; (f) Takahashi, H.; Kashiwa, N.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2002, 43, 2935; (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284; (h) Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338; (i) Loh, T.-P.; Chen, S.-L. Org. Lett. 2002, 4, 3647; (j) Akiyama, T.; Ito, J.; Fuchibe, K. Synlett 2002, 1269; (k) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
14. Recent examples of Mannich-type reactions, see: (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143; (b) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463; (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983; (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640; (e) Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652; (f) Takahashi, H.; Kashiwa, N.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2002, 43, 2935; (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284; (h) Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338; (i) Loh, T.-P.; Chen, S.-L. Org. Lett. 2002, 4, 3647; (j) Akiyama, T.; Ito, J.; Fuchibe, K. Synlett 2002, 1269; (k) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
15. Recent examples of Mannich-type reactions, see: (a) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143; (b) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463; (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983; (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640; (e) Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652; (f) Takahashi, H.; Kashiwa, N.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2002, 43, 2935; (g) Muraoka, T.; Kamiya, S.; Matsuda, I.; Itoh, K. Chem. Commun. 2002, 1284; (h) Akiyama, T.; Takaya, J.; Kagoshima, H. Adv. Synth. Catal. 2002, 344, 338; (i) Loh, T.-P.; Chen, S.-L. Org. Lett. 2002, 4, 3647; (j) Akiyama, T.; Ito, J.; Fuchibe, K. Synlett 2002, 1269; (k) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
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