Synthesis of tricyclic phosphonopyrrolidines via IMDAF: Experimental and theoretical investigation of the observed stereoselectivity

Journal of Organic Chemistry

Volumn 73, Issue 20, 2008, Pages 7921-7927

  Claeys, Diederica D ^a   Moonen, Kristof ^a   Roman, Bart I ^a   Nemykin, Victor N ^b   Zhdankin, Viktor V ^b   Waroquier, Michel ^a   Van Speybroeck, Veronique ^a   Stevens, Christian V ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF MINNESOTA DULUTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC SPECTROSCOPY; CHEMICAL REACTIONS; DENSITY FUNCTIONAL THEORY; ISOMERS; PROBABILITY DENSITY FUNCTION; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

CARBONYL GROUPS; CHEMICAL EQUATIONS; DENSITY FUNCTIONAL THEORY METHODS; EPIMERS; HARTREE-FOCK; INTRAMOLECULAR DIELS-ALDER REACTIONS; PHOSPHONATE; PHOSPHONATES; RAY ANALYSIS; SMALL ENERGIES; SPECTROSCOPIC DATA; STERIC HINDRANCES; SYNTHESIS OF; TRANSITION STATES;

TETHERLINES;

1 ACYLAMINO(FURAN 2 YL)METHYLPHOSPHONATE; CARBONYL DERIVATIVE; FURAN; METHYLPHOSPHONIC ACID; PHOSPHONIC ACID DERIVATIVE; PHOSPHONOPYRROLIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; EXPERIMENTAL STUDY; ISOMER; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; THEORETICAL STUDY; THERMODYNAMICS; X RAY ANALYSIS;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; PHOSPHONIC ACIDS; PYRROLIDINES; STEREOISOMERISM; THERMODYNAMICS;

EID: 53849111969     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801138s     Document Type: Article

References (72)

1. Kafarski, P.; Lejczak, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 63, 193-215, and references therein.
2. (a) Moonen, K.; Laureyn, I.; Stevens, C. V. Chem. Rev. 2004, 104, 6177-6215.
3. (b) Redmore, D. Chem. Rev. 1971, 71, 315-337.
4. (c) Robiette, R.; Defacqz, N.; Peeters, D.; Marchand-Brynaert, J. Curr. Org. Synth. 2005, 2, 453-477.
5. (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795-819.
6. (b) Wenkert, E.; Moeller, P. D. R.; Piettre, S. R. J. Am. Chem. Soc. 1988, 110, 7188-7194.
7. (c) Domingo, L. R.; Picher, M. T.; Aurell, M. J. J. Phys. Chem. A 1999, 103, 11425-11430.
8. (d) Lautens, M.; Fillion, E. J. Org. Chem. 1996, 61, 7994-7995.
9. Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233.
10. (a) Zhang, H. J.; Padwa, A. Org. Lett. 2006, 8, 247-250.
11. (b) Padwa, A.; Ginn, J. D. J. Org. Chem. 2005, 70, 5197-5206.
12. (c) Wang, Q.; Padwa, A. Org. Lett. 2004, 6, 2189-2192.
13. (d) Kouznetsov, V. V.; Zubkov, F. I.; Cruz, U. M.; Voskressensky, L. G.; Mendez, L. Y. V.; Astudillo, L.; Stashenko, E. E. Lett. Org. Chem. 2004, 1, 37-39.
14. (e) Fokas, D.; Patterson, J. E.; Slobodkin, G.; Baldino, C. M. Tetrahedron Lett. 2003, 44, 5137-5140.
15. (f) Padwa, A.; Eidell, C. K.; Lynch, S. M. Heterocycles 2002, 58, 227-242.
16. (g) Padwa, A.; Dimitroff, M.; Liu, B. Org. Lett. 2000, 2, 3233-3235.
17. (h) Sprague, P. W.; Heikes, J. E.; Gougoutas, J. Z.; Malley, M. F.; Harris, D. N.; Greenberg, R. J. Med. Chem. 1985, 28, 1580-1590.
18. (i) Sneden, A. T. Synlett 1993, 5, 313-322.
19. (j) Yu, S. Y.; Beese, G.; Keay, B. A. J. Chem. Soc., Perkin Trans. 1 1992, 2729-2731.
20. Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521-13624.
21. (a) Namboothiri, I. N. N.; Ganesh, M.; Mobin, S. M.; Cojocaru, M. J. Org. Chem. 2005, 70, 2235-2243.
22. (b) Zubkov, F. I.; Boltukhina, E. V.; Turchin, K. F.; Borisov, R. S.; Varlamov, A. V. Tetrahedron 2005, 61, 4099-4113.
23. (c) Varlamov, A. V.; Zubkov, F. I.; Boltukhina, E. V.; Sidorenko, N. V.; Borisov, R. S. Tetrahedron Lett. 2003, 44, 3641-3643.
24. (a) Weingarten, M. D.; Prein, M.; Price, A. T.; Snyder, J. P.; Padwa, A. J. Org. Chem. 1997, 62, 2001-2010.
25. (b) Turner, C. I.; Williamson, R. M.; Paddon-Row, M. N.; Sherburn, M. S. J. Org. Chem. 2001, 66, 3963-3969.
26. (c) Tantillo, D. J.; Houk, K. N.; Jung, M. E. J. Org. Chem. 2001, 66, 1938-1940.
27. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232.
28. Bur, S. K.; Lynch, S. M.; Padwa, A. Org. Lett. 2002, 4, 473-476.
29. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
30. (b) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frish, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
31. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675.
32. (a) Zhao, Y.; Lynch, B. J.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 2715-2719.
33. (b) BB95/6-31+G(d) 1Op(3/76=0580004200).
34. (a) Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503-506.
35. (b) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 275-280.
36. (c) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 281-289.
37. (d) Head-Gordon, M.; Head-Gordon, T. Chem. Phys. Lett. 1994, 220, 122-128.
38. (e) Saebo, S.; Almlof, J. Chem. Phys. Lett. 1989, 154, 83-89.
39. (a) Pople, J. A.; Seeger, R.; Krishnan, R. Int. J. Quant. Chem. Symp. 1977, 11, 149-163.
40. (b) Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quant. Chem. Symp. 1976, 10, 1-19.
41. (a) Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, 14, 545-560.
42. (b) Bartlett, R. J.; Purvis, G. D. J. Quant. Chem. 1978, 14, 561-581.
43. (c) Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918.
44. (d) Scuseria, G. E.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1988, 89, 7382-7387.
45. (e) Scuseria, G. E.; Schaefer, H. F., III. J. Chem. Phys. 1989, 90, 3700-3703.
46. (a) Van Speybroeck, V.; Moonen, K.; Hemelsoet, K.; Stevens, C. V.; Waroquier, M. J. Am. Chem. Soc. 2006, 128, 8468-8478.
47. (b) Stevens, C. V.; Vekemans, W.; Moonen, K.; Rammeloo, T. Tetrahedron Lett. 2003, 44, 1619-1622.
48. (c) Moonen, K.; Stevens, C. V. Synthesis 2005, 3603-3612.
49. Van Meenen, E.; Moonen, K.; Acke, D.; Stevens, C. V. Arkivoc 2006, i, 31-45.
50. Ghelfi, F.; Parsons, A. F.; Tommasini, D.; Mucci, A. Eur. J. Org. Chem. 2001, 1845-1852.
51. (a) Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858-5865.
52. (b) Parrill, A. L.; Dolata, D. P. THEOCHEM 1996, 370, 187-202.
53. (a) Pedrosa, R.; Sayalero, S.; Vicente, M.; Casado, B. J. Org. Chem. 2005, 70, 7273-7278.
54. (b) Padwa, A.; Ginn, J. D.; Bur, S. K.; Eidell, C. K.; Lynch, S. M. J. Org. Chem. 2002, 67, 3412-3424.
55. (c) Paulvannan, K.; Chen, T.; Jacobs, J. W. Synlett 1999, 1609-1611.
56. Tromp, R. A.; Brussee, J.; van der Gen, A. Org. Biomol. Chem. 2003, 1, 3592-3599.
57. (a) Feringa, B. L.; Gelling, O. J.; Melters, L. Tetrahedron Lett. 1990, 31, 7201-7204.
58. (b) Van Royen, L. A.; Mijngheer, R.; De Clercq, P. J. Tetrahedron Lett. 1983, 24, 3145-3148.
59. (a) Kong, S.; Evanseck, J. D. J. Am. Chem. Soc. 2000, 122, 10418-10427.
60. (b) Moreau, Y.; Loos, P.-F.; Assfeld, X. Theor. Chem. Acc. 2004, 112, 228-239.
61. (c) Acevedo, O.; Jorgensen, W. L. J. Chem. Theory Comput. 2007, 3, 1412-1419.
62. Frish, M. J. et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford; CT, 2004; see the Supporting Information for the full reference.
63. (a) Leyssens, T.; Peeters, D. THEOCHEM 2004, 673, 79-86.
64. (b) Leyssens, T.; Peeters, D. THEOCHEM 2004, 686, 71-82.
65. Guner, V.; Khuong, K. S.; Leach, A. G.; Lee, P. S.; Bartberger, M. D.; Houk, K. N. J. Phys. Chem. A 2003, 107, 11445-11459.
66. (a) Domingo, L. R.; Aurell, M. J.; Arno, M.; Saez, J. A. J. Org. Chem. 2007, 72, 4220-4227.
67. (b) Pieniazek, S. N.; Houk, K. N. Angew. Chem. 2006, 118, 1470-1473.
68. (c) Pieniazek, S. N.; Houk, K. N. Angew. Chem., Int. Ed. 2006, 45, 1442-1445.
69. (d) Padwa, A.; Crawford, K. R.; Straub, C. S.; Pieniazek, S. N.; Houk, K. N. J. Org. Chem. 2006, 71, 5432-5439.
70. (e) Dinadayalane, T. C.; Vijaya, R.; Smitha, A.; Sastry, G. N. J. Phys. Chem. A 2002, 106, 1627-1633.
71. (f) Domingo, L. R.; Picher, M. T.; Andrés, J. J. Org. Chem. 2000, 65, 3473-3477.
72. Seeman, J. I. Chem. Rev. 1983, 2, 83-134.