Cycloaddition Reactions of Chiral 2-Amino-1,3-butadienes with Nitroalkenes: Synthesis of Enantiomerically Pure 4-Nitrocyclohexanones

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6746-6753

  Barluenga, José ^a   Aznar, Fernando ^a   Ribas, Cristina ^a   Valdés, Carlos ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000965115     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970237m     Document Type: Article

References (62)

1. A communication containing preliminary results on this work has been previously published: Barluenga, J.; Aznar, F.; Valdés, C.; Martín, A.; García-Granda, S.; Martín, E. J. Am. Chem. Soc. 1993, 115, 4403-4404.
2. For recent reviews on catalytic asymmetric Diels-Alder reactions, see: (a) Kagan, B. H.; Riant, O. Chem. Rev. 1992, 92, 1007. (b) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (c) Seyden-Penne, J. Chiral Auxiliares and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; pp 537-553. For some leading articles, see: (d) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049. (f) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502 and references cited therein.
3. For recent reviews on catalytic asymmetric Diels-Alder reactions, see: (a) Kagan, B. H.; Riant, O. Chem. Rev. 1992, 92, 1007. (b) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (c) Seyden-Penne, J. Chiral Auxiliares and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; pp 537-553. For some leading articles, see: (d) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049. (f) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502 and references cited therein.
4. For recent reviews on catalytic asymmetric Diels-Alder reactions, see: (a) Kagan, B. H.; Riant, O. Chem. Rev. 1992, 92, 1007. (b) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (c) Seyden-Penne, J. Chiral Auxiliares and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; pp 537-553. For some leading articles, see: (d) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049. (f) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502 and references cited therein.
5. For recent reviews on catalytic asymmetric Diels-Alder reactions, see: (a) Kagan, B. H.; Riant, O. Chem. Rev. 1992, 92, 1007. (b) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (c) Seyden-Penne, J. Chiral Auxiliares and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; pp 537-553. For some leading articles, see: (d) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049. (f) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502 and references cited therein.
6. For recent reviews on catalytic asymmetric Diels-Alder reactions, see: (a) Kagan, B. H.; Riant, O. Chem. Rev. 1992, 92, 1007. (b) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (c) Seyden-Penne, J. Chiral Auxiliares and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; pp 537-553. For some leading articles, see: (d) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049. (f) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502 and references cited therein.
7. For recent reviews on catalytic asymmetric Diels-Alder reactions, see: (a) Kagan, B. H.; Riant, O. Chem. Rev. 1992, 92, 1007. (b) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497. (c) Seyden-Penne, J. Chiral Auxiliares and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; pp 537-553. For some leading articles, see: (d) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. (e) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049. (f) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502 and references cited therein.
8. For leading references on the use of chiral dienophiles in asymmetric Diels-Alder reactions, see: (a) Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. (b) Evans, D. A.; Chapman, K. T.; Bisasha, J. J. Am. Chem. Soc. 1988, 110, 1238. (c) Oppolzer, W. Camphor derivatives as Chiral Auxiliares in Asymmetric Synthesis. Tetrahedron 1987, 43, 1969. (d) Oppolzer, W.; Willis, M.; Kelly, M. J.; Signer, M.; Blagg, J. Tetrahedron Lett. 1990, 31, 5015.
9. For leading references on the use of chiral dienophiles in asymmetric Diels-Alder reactions, see: (a) Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. (b) Evans, D. A.; Chapman, K. T.; Bisasha, J. J. Am. Chem. Soc. 1988, 110, 1238. (c) Oppolzer, W. Camphor derivatives as Chiral Auxiliares in Asymmetric Synthesis. Tetrahedron 1987, 43, 1969. (d) Oppolzer, W.; Willis, M.; Kelly, M. J.; Signer, M.; Blagg, J. Tetrahedron Lett. 1990, 31, 5015.
10. For leading references on the use of chiral dienophiles in asymmetric Diels-Alder reactions, see: (a) Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. (b) Evans, D. A.; Chapman, K. T.; Bisasha, J. J. Am. Chem. Soc. 1988, 110, 1238. (c) Oppolzer, W. Camphor derivatives as Chiral Auxiliares in Asymmetric Synthesis. Tetrahedron 1987, 43, 1969. (d) Oppolzer, W.; Willis, M.; Kelly, M. J.; Signer, M.; Blagg, J. Tetrahedron Lett. 1990, 31, 5015.
11. For leading references on the use of chiral dienophiles in asymmetric Diels-Alder reactions, see: (a) Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. (b) Evans, D. A.; Chapman, K. T.; Bisasha, J. J. Am. Chem. Soc. 1988, 110, 1238. (c) Oppolzer, W. Camphor derivatives as Chiral Auxiliares in Asymmetric Synthesis. Tetrahedron 1987, 43, 1969. (d) Oppolzer, W.; Willis, M.; Kelly, M. J.; Signer, M.; Blagg, J. Tetrahedron Lett. 1990, 31, 5015.
12. For review on chiral dienes, see: (a) Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlights; VCH Verlagsgesellschaft: Weinheim, 1991; pp 60-61. (b) Seyden-Penne, J. Chiral Auxiliares and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; pp 586-593.
13. For review on chiral dienes, see: (a) Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlights; VCH Verlagsgesellschaft: Weinheim, 1991; pp 60-61. (b) Seyden-Penne, J. Chiral Auxiliares and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; pp 586-593.
14. For some leading references on C1-substituted chiral dienes, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595-7596. (b) Larsen, D. S.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1990, 1339-1352. (c) Gree, R.; Kessabi, L.; Mosset, P.; Martelli, J.; Carrie, R. Tetrahedron Lett. 1984, 25, 3697. (d) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633. (e) Datta, S. C.; Franck, R. W.; Tripathy, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472-8478. (f) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630-7640. (g) Arce, F.; Carreño, M. C.; Cid, M. B.; García-Ruano, J. L. J. Org. Chem. 1994, 59, 3421 and references cited therein.
15. For some leading references on C1-substituted chiral dienes, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595-7596. (b) Larsen, D. S.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1990, 1339-1352. (c) Gree, R.; Kessabi, L.; Mosset, P.; Martelli, J.; Carrie, R. Tetrahedron Lett. 1984, 25, 3697. (d) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633. (e) Datta, S. C.; Franck, R. W.; Tripathy, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472-8478. (f) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630-7640. (g) Arce, F.; Carreño, M. C.; Cid, M. B.; García-Ruano, J. L. J. Org. Chem. 1994, 59, 3421 and references cited therein.
16. For some leading references on C1-substituted chiral dienes, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595-7596. (b) Larsen, D. S.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1990, 1339-1352. (c) Gree, R.; Kessabi, L.; Mosset, P.; Martelli, J.; Carrie, R. Tetrahedron Lett. 1984, 25, 3697. (d) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633. (e) Datta, S. C.; Franck, R. W.; Tripathy, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472-8478. (f) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630-7640. (g) Arce, F.; Carreño, M. C.; Cid, M. B.; García-Ruano, J. L. J. Org. Chem. 1994, 59, 3421 and references cited therein.
17. For some leading references on C1-substituted chiral dienes, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595-7596. (b) Larsen, D. S.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1990, 1339-1352. (c) Gree, R.; Kessabi, L.; Mosset, P.; Martelli, J.; Carrie, R. Tetrahedron Lett. 1984, 25, 3697. (d) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633. (e) Datta, S. C.; Franck, R. W.; Tripathy, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472-8478. (f) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630-7640. (g) Arce, F.; Carreño, M. C.; Cid, M. B.; García-Ruano, J. L. J. Org. Chem. 1994, 59, 3421 and references cited therein.
18. For some leading references on C1-substituted chiral dienes, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595-7596. (b) Larsen, D. S.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1990, 1339-1352. (c) Gree, R.; Kessabi, L.; Mosset, P.; Martelli, J.; Carrie, R. Tetrahedron Lett. 1984, 25, 3697. (d) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633. (e) Datta, S. C.; Franck, R. W.; Tripathy, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472-8478. (f) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630-7640. (g) Arce, F.; Carreño, M. C.; Cid, M. B.; García-Ruano, J. L. J. Org. Chem. 1994, 59, 3421 and references cited therein.
19. For some leading references on C1-substituted chiral dienes, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595-7596. (b) Larsen, D. S.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1990, 1339-1352. (c) Gree, R.; Kessabi, L.; Mosset, P.; Martelli, J.; Carrie, R. Tetrahedron Lett. 1984, 25, 3697. (d) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633. (e) Datta, S. C.; Franck, R. W.; Tripathy, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472-8478. (f) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630-7640. (g) Arce, F.; Carreño, M. C.; Cid, M. B.; García-Ruano, J. L. J. Org. Chem. 1994, 59, 3421 and references cited therein.
20. For some leading references on C1-substituted chiral dienes, see: (a) Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595-7596. (b) Larsen, D. S.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1990, 1339-1352. (c) Gree, R.; Kessabi, L.; Mosset, P.; Martelli, J.; Carrie, R. Tetrahedron Lett. 1984, 25, 3697. (d) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633. (e) Datta, S. C.; Franck, R. W.; Tripathy, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472-8478. (f) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630-7640. (g) Arce, F.; Carreño, M. C.; Cid, M. B.; García-Ruano, J. L. J. Org. Chem. 1994, 59, 3421 and references cited therein.
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43. 1H NMR], derived from the reaction of the chiral diene with two molecules of 2-nitro-1-propene.
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46. 1 = TBDMS) was reacted with 2-methyl-1-nitro-1-propene under the Standard conditions, no reaction product was observed and the starting materials were recovered.
47. In our previous paper dedicated to the reaction of nonchiral 2-amino dienes with β-nitrostyrene (see ref 14), we observed that very polar solvents such as MeOH favor the cyclization process, giving rise to a single diastereoisomer. However, less polar solvents like THF or chloroform lead to a mixture of three compounds: two diastereoisomers of nitrocyclohexanone and the open chain compound derived from the Michael type addition of the enamine to the electrophilic double bond.
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50. Enantiomeric excesses were determined from furans 7 and not from open chain compounds 6 due to the unstability of the latter. Upon standing, compounds 6 undergo isomerization of the Z double bond.
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