Construction of carbocyclic arrays containing nitrogen via intramolecular imino Diels-Alder reactions in polar media. A comparative study: 5.0 M lithium perchlorate-diethyl ether versus water

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 6041-6048

  Grieco, Paul A ^a   Kaufman, Michael D ^b  

^a MONTANA STATE UNIVERSITY   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER; LITHIUM PERCHLORATE; NITROGEN; PERCHLORATE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CONCENTRATION (PARAMETERS); CYCLIZATION; DIASTEREOISOMER; ISOMERISM; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE;

EID: 0033529842     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9905930     Document Type: Article

References (28)

1. Grieco, P. A. Aldrichim. Acta 1991, 24, 59. Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakürek, V., Ed.; VCH: Basel, 1993; p 133. Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
2. Grieco, P. A. Aldrichim. Acta 1991, 24, 59. Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakürek, V., Ed.; VCH: Basel, 1993; p 133. Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
3. Grieco, P. A. Aldrichim. Acta 1991, 24, 59. Grieco, P. A. Organic Chemistry in Lithium Perchlorate/Diethyl Ether. In Organic Chemistry: Its Language and Its State of the Art; Kisakürek, V., Ed.; VCH: Basel, 1993; p 133. Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
4. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
5. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
6. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
7. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
8. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
9. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
10. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
11. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
12. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
13. For the use of concentrated solutions of lithium perchlorate in diethyl ether to promote Diels-Alder reactions, see: Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. Grieco, P. A.; Moher, E. D. Tetrahedron Lett. 1993, 34, 5567. Grieco, P. A.; Beck, J. P. Tetrahedron Lett. 1993, 34, 7367. Grieco, P. A.; Handy, S. T.; Beck, J. P. Tetrahedron Lett. 1994, 35, 2663. Grieco, P. A.; Beck, J. P.; Handy, S. T.; Saito, N.; Daeuble, J. F. Tetrahedron Lett. 1994, 35, 6783. Grieco, P. A.; Piñeiro-Nuñez, M. M. J. Am. Chem. Soc. 1994, 116, 7606. Grieco, P. A.; Kaufman, M. D.; Daeuble, J. F.; Saito, N. J. Am. Chem. Soc., 1996, 118, 2095. May, S. A.; Grieco, P. A.; Lee, H. H. Synlett 1997, 493. Grieco, P. A.; Dai, Y. J. Am. Chem. Soc. 1998, 120, 5128. Grieco, P. A.; Kaufman, M. D. Tetrahedron Lett. 1999, 40, 1265.
14. For the use of water in the promotion of imino Diels-Alder reactions, see: Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658.
15. For the use of water in the promotion of imino Diels-Alder reactions, see: Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658.
16. For the use of water in the promotion of imino Diels-Alder reactions, see: Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658.
17. For the use of water in the promotion of imino Diels-Alder reactions, see: Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658.
18. For the use of water in the promotion of imino Diels-Alder reactions, see: Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. Grieco, P. A.; Larsen, S. D.; Forbare, W. F. Tetrahedron Lett. 1986, 27, 1975. Grieco, P. A.; Larsen, S. D. J. Org. Chem. 1986, 51, 3553. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3658.
19. 6 to 3.0 M lithium perchlorate in diethyl ether containing 10 mol % trifluroacetic acid gave rise to lactam 35 in 55% yield. (equation presented)
20. Substrate 3 was prepared via a one-pot procedure. Treatment of δ-valerolactone with 2.0 equiv of n-butyllithium followed by sequential addition of 1-iodo-hepta-4(E),6-diene (33) and di-tert-butyl dicarbonate provided lactam 34 (see the Experimental Section).
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22. For an intermolecular N-(acyloxy)iminium ion-olefin cyclo- addition, see: Ben-Ishai, D.; Hirsch, S. Tetrahedron Lett. 1983, 24, 955. For an intramolecular example see: Fisher, M. J.; Overman, L. E. J. Org. Chem. 1990, 55, 1447.
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