Lanthanide(III)-catalyzed multi-component aza-Diels-Alder reaction of aliphatic N-arylaldimines with cyclopentadiene

Tetrahedron Letters

Volumn 44, Issue 41, 2003, Pages 7569-7573

  Powell, David A ^a   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Aza Diels Alder; Lanthanides; Multi component coupling; Povarov reaction; Quinolines

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; HETEROCYCLIC COMPOUND; IMINE; LANTHANIDE; TETRAHYDROQUINAZOLINE DERIVATIVE;

ARTICLE; CATALYST; DIELS ALDER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY;

BETULACEAE;

EID: 0141518222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.066     Document Type: Article

References (38)

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4. For a few leading references see: (a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858; (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259-266; (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132; (d) Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 54, 5089-5096; (e) Posson, H.; Hurvois, J.-P.; Moinet, C. Synlett 2000, 209-212; (f) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P. T. Synthesis 2000, 661-666; (g) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363; (h) Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219; (i) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414; (j) Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717-720.
5. For a few leading references see: (a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858; (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259-266; (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132; (d) Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 54, 5089-5096; (e) Posson, H.; Hurvois, J.-P.; Moinet, C. Synlett 2000, 209-212; (f) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P. T. Synthesis 2000, 661-666; (g) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363; (h) Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219; (i) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414; (j) Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717-720.
6. For a few leading references see: (a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858; (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259-266; (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132; (d) Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 54, 5089-5096; (e) Posson, H.; Hurvois, J.-P.; Moinet, C. Synlett 2000, 209-212; (f) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P. T. Synthesis 2000, 661-666; (g) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363; (h) Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219; (i) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414; (j) Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717-720.
7. For a few leading references see: (a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858; (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259-266; (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132; (d) Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 54, 5089-5096; (e) Posson, H.; Hurvois, J.-P.; Moinet, C. Synlett 2000, 209-212; (f) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P. T. Synthesis 2000, 661-666; (g) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363; (h) Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219; (i) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414; (j) Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717-720.
8. For a few leading references see: (a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858; (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259-266; (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132; (d) Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 54, 5089-5096; (e) Posson, H.; Hurvois, J.-P.; Moinet, C. Synlett 2000, 209-212; (f) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P. T. Synthesis 2000, 661-666; (g) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363; (h) Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219; (i) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414; (j) Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717-720.
9. For a few leading references see: (a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858; (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259-266; (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132; (d) Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 54, 5089-5096; (e) Posson, H.; Hurvois, J.-P.; Moinet, C. Synlett 2000, 209-212; (f) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P. T. Synthesis 2000, 661-666; (g) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363; (h) Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219; (i) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414; (j) Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717-720.
10. For a few leading references see: (a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858; (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259-266; (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132; (d) Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 54, 5089-5096; (e) Posson, H.; Hurvois, J.-P.; Moinet, C. Synlett 2000, 209-212; (f) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P. T. Synthesis 2000, 661-666; (g) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363; (h) Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219; (i) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414; (j) Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717-720.
11. For a few leading references see: (a) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858; (b) Lucchini, V.; Prato, M.; Scorrano, G.; Stivanello, M.; Valle, G. J. Chem. Soc., Perkin Trans. 2 1992, 259-266; (c) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132; (d) Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 54, 5089-5096; (e) Posson, H.; Hurvois, J.-P.; Moinet, C. Synlett 2000, 209-212; (f) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P. T. Synthesis 2000, 661-666; (g) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362-2363; (h) Spanedda, M. V.; Hoang, V. D.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. Tetrahedron Lett. 2003, 44, 217-219; (i) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414; (j) Lavilla, R.; Bernabeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717-720.
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37. 3N (the use of base treated silica gel ensures reproducible yields and minimizes acid promoted oxidation to quinolines).
38. 5) in 88% yield. These results mirror those of Fang and co-workers (Ref. 10a).