The Lewis acids catalyzed aza-Diels-Alder reaction of methylenecyclopropanes with imines

Organic Letters

Volumn 5, Issue 4, 2003, Pages 579-582

  Shi, Min ^a   Shao, Li Xiong ^a   Xu, Bo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; IMINE; LEWIS ACID; PROPANE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; DIELS ALDER REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0141741420     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0275365     Document Type: Article

References (27)

1. For a recent review see: Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 2, 111. For synthesis of MCPssee: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 598.
2. For a recent review see: Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 2, 111. For synthesis of MCPssee: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 598.
3. (a) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365.
4. (b) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270.
5. Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458.
6. Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123.
7. (a) Inoue, Y.; Hibi, T.; Sataka, H.; Hashimoto, H. J. Chem. Soc., Chem. Commun. 1979, 982.
8. (b) Binger, P.; Germer, A. Chem. Ber. 1984, 114, 3325.
9. Nakamura, I.; Oh, B. H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
10. Oh, B. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203.
11. Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069.
12. Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676.
13. Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790.
14. Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015.
15. Chatani, N.; Takaya, H.; Hanafusa, T. Tetrahedron Lett. 1988, 29, 3979.
16. The reaction of reactions of MCPs with unsaturated carbon bonds had been extensively studied; please see the following review: Laurens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
17. (a) The Lewis acid-catalyzed ring-opening reactions of MCPs: Shi, M.; Xu, B. Org. Lett., 2002, 4, 2145 and references therein.
18. (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019.
19. The papers related aza-Diels-Alder reactions of dienophiles (cyclopentadienes, vinyl sulfides, or vinyl ethers) with imines. Please see: (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (b) Yadav, J. S.; Reddy, B. V. S.; Madhuri, C. R.; Sabitha, G. Synthesis 2001, 1065. (c) Nagarajan, R.; Perumal, P. T. Synth. Commun. 2001, 31, 1733. (d) Anniyappan, M. ; Nagarajan, R.; Perumal, P. T. Synth. Commun. 2002, 32, 99.
20. The papers related aza-Diels-Alder reactions of dienophiles (cyclopentadienes, vinyl sulfides, or vinyl ethers) with imines. Please see: (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (b) Yadav, J. S.; Reddy, B. V. S.; Madhuri, C. R.; Sabitha, G. Synthesis 2001, 1065. (c) Nagarajan, R.; Perumal, P. T. Synth. Commun. 2001, 31, 1733. (d) Anniyappan, M. ; Nagarajan, R.; Perumal, P. T. Synth. Commun. 2002, 32, 99.
21. The papers related aza-Diels-Alder reactions of dienophiles (cyclopentadienes, vinyl sulfides, or vinyl ethers) with imines. Please see: (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (b) Yadav, J. S.; Reddy, B. V. S.; Madhuri, C. R.; Sabitha, G. Synthesis 2001, 1065. (c) Nagarajan, R.; Perumal, P. T. Synth. Commun. 2001, 31, 1733. (d) Anniyappan, M. ; Nagarajan, R.; Perumal, P. T. Synth. Commun. 2002, 32, 99.
22. The papers related aza-Diels-Alder reactions of dienophiles (cyclopentadienes, vinyl sulfides, or vinyl ethers) with imines. Please see: (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (b) Yadav, J. S.; Reddy, B. V. S.; Madhuri, C. R.; Sabitha, G. Synthesis 2001, 1065. (c) Nagarajan, R.; Perumal, P. T. Synth. Commun. 2001, 31, 1733. (d) Anniyappan, M. ; Nagarajan, R.; Perumal, P. T. Synth. Commun. 2002, 32, 99.
23. -1. Diffractometer: Rigaku AFC7R. Residuals: R = 0.0629, Rw = 0.1508.
24. w, = 0.0635.
25. 1H NMR spectroscopic data. Please see: Primke, H.; Satin, G. S.; Kohlstruk, S.; Adiwidjaja, G.; de Meijere, A. Chem. Ber. 1994, 127, 1051.
26. Kobayashi has concluded that this type of aza-Diels-Alder reaction proceeds via a stepwise mechanism. Please see ref 16a.
27. The rearrangement of cyclopropylmethyl cation has already been studied extensively. It is reasonable that the substituents on the double bond further stabilize the cation. Please see: Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 5th ed.; Plenum Press: New York, 1998; pp 221 and 419.