Diastereo- and regioselectivity in Diels-Alder reaction of [1,4,2]diazaphospholo[4,5-a]pyridines

Tetrahedron

Volumn 61, Issue 44, 2005, Pages 10521-10528

  Bansal, Raj K ^a   Karaghiosoff, Konstantin ^b   Gupta, Neelima ^a   Gandhi, Neelam ^a   Kumawat, Surendra K ^a  

^a UNIVERSITY OF RAJASTHAN   (India)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

Azaphospholes; DFT calculations; Diastereoselectivity; Diels Alder reaction; Regioselectivity

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 2,3 DIMETHYLBUTADIENE; ISOPRENE; METHYL IODIDE; NITROGEN; PYRIDINE DERIVATIVE; SELENIUM; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; DIELS ALDER REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 25844489020     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.045     Document Type: Article

References (51)

1. W. Carruthers Cycloaddition Reactions in Organic Synthesis Tetrahedron Organic Chemistry Series 1990 Pergamon Elmsford, NY
2. L. Borger, and S.N. Weinberg Hetero Diels-Alder Methodology in Organic Synthesis 1987 Academic New York
3. J.D. Winkler Chem. Rev. 96 1996 167
4. I. Fleming Frontier Orbitals and Organic Chemical Reactions 1976 Wiley New York
5. A. Ponti J. Phys. Chem. A 104 2000 8843
6. S.C. Pellegrinet, M.A. Silva, and J.M. Goodman J. Am. Chem. Soc. 123 2001 8832
7. C.P. Dell J. Chem. Soc., Perkin Trans. 1 1998 3873 and references cited therein
8. R. Appel, F. Knoll, and I. Ruppert Angew. Chem., Int. Ed. Engl. 20 1981 731
9. R. Appel Pure Appl. Chem. 59 1987 977
10. B. Weber, and M. Regitz M. Regitz Methods in Organic Chemistry (Houben-Weyl) Vol. 4 1982 Thieme Stuttgart 27 Part E 1
11. L.N. Markovskii, and V.D. Romanenko Tetrahedron 45 1989 6019
12. A. Schmidpeter, and K. Karaghiosoff M. Regitz O.J. Scherer Multiple Bonds and Low Coordination in Phosphorus Chemistry 1990 Thieme Stuttgart 258
13. A. Schmidpeter p 709, see also p 715; Vol. 4, p 771 A.R. Katritzky C.W. Rees E.F.V. Scriven Comprehensive Heterocyclic Chemistry-II Vol. 3 1996 Pergamon Oxford 709
14. A. Schmidpeter F. Mathey Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain 2001 Elsevier Amsterdam 363
15. R.K. Bansal, K. Karaghiosoff, and A. Schmidpeter Tetrahedron 50 1994 7675
16. R.K. Bansal, K. Karaghiosoff, N. Gandhi, and A. Schmidpeter Synthesis 1995 361
17. R.K. Bansal, R. Mahnot, G. Pandey, and R. Gupta J. Indian Chem. Soc. 71 1995 415
18. R.K. Bansal, and J. Heinicke Chem. Rev. 101 2001 3549
19. R.K. Bansal, and N. Gupta R.C. Storr T.L. Gilchrist Science of Synthesis: Methods of Molecular Transformations (Houben-Weyl) Vol. 13 2004 Thieme Stuttgart 647 see also p 689, 743
20. G. Märkl M. Regitz Methods in Organic Chemistry (Houben-Weyl) Vol.4 1982 Thieme Stuttgart 72 Part E1
21. G. Märkl M. Regitz O.J. Scherer Multiple Bonds and Low Coordination in Phosphorus Chemistry 1990 Thieme Stuttgart 220
22. S.M. Bachrach, and M. Liu J. Org. Chem. 57 1992 6736
23. C.S. Wannere, R.K. Bansal, and P.v.R. Schleyer J. Org. Chem. 67 2002 9162
24. R.K. Bansal, L. Hemrajani, and N. Gupta Heteroat. Chem. 10 1999 598
25. R.K. Bansal, V.K. Jain, N. Gupta, N. Gupta, L. Hemrajani, M. Baweja, and P.G. Jones Tetrahedron 58 2002 1573
26. R.K. Bansal, A. Dandia, N. Gupta, and D. Jain Heteroat. Chem. 14 2003 560
27. R.K. Bansal, K. Karaghiosoff, N. Gupta, V. Kabra, R. Mahnot, D.C. Sharma, R. Munjal, and S.K.Z. Kumawat Naturforsch. 60b 2005 7
28. J. Heinicke, and A. Tzschach Tetrahedron Lett. 24 1983 5481
29. Y.Y.C. Yeung Lam Ko, R. Carrie, L. Toupet, and F. De Sarlo Bull. Soc. Chim. Fr. 1986 115
30. R. Chen, B. Cai, and G. Li Synthesis 1991 783
31. K. Karaghiosoff, R. Mahnot, C. Cleve, N. Gandhi, R.K. Bansal, and A. Schmidpeter Chem. Ber. 128 1995 581
32. K. Karaghiosoff, R.K. Bansal, and N.Z. Gupta Naturforsch. 47b 1992 373
33. K. Karaghiosoff, C. Cleve, and A. Schmidpeter Phosphorus Sulfur 28 1986 289
34. H.R. Hudson, K.B. Dillon, and B.J. Walker J.C. Tebby CRC Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data 1991 CRC Boca Raton, Florida 181
35. 13P-NMR Spektroskopie Vol. 3 1993 Thieme Stuttgart p 133
36. Y. Leroux, R. Burgada, G. Kleeman, and E. Fluck J.C. Tebby CRC Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data 1991 CRC Boca Raton, Florida 93
37. W.G. Bentrude, and W.N. Setzer J.G. Verkade L.D. Quin Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis 1987 VCH Florida 365
38. L.R. Domingo, M. Arnó, and J. Andrés J. Org. Chem. 64 1999 5867
39. D. Margetic, M.R. Johnston, and R.N. Warrener Molecules 5 2001 1417
40. L.R. Domingo, M. Oliva, and J. Andrés J. Org. Chem. 66 2001 6151
41. L.R. Domingo, and M.J. Aurell J. Org. Chem. 67 2002 959
42. L.R. Domingo Tetrahedron 58 2002 3765
43. L.R. Domingo, M.J. Aurell, P. Pérez, and R. Contreras J. Phys. Chem. A 106 2002 6871
44. M.A. Silva, S.C. Pellegrinet, and J.M. Goodman J. Org. Chem. 68 2003 4059
45. M.A. Silva, S.C. Pellegrinet, and J.M. Goodman ARKIVOC 2003 556
46. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.; NBO Version 3.1, vide Gaussian 03 User's Reference, 2003, p 3.
47. J.E. Carpenter, and F. Weinhold J. Mol. Struct. (Theochem) 169 1988 41
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A., Gaussian 03, Revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
49. L.R. Domingo, M. Arnó, R. Contreras, and P. Pérez J. Phys. Chem. A 106 2002 952
50. E. Cancés, B. Mennuci, and J. Tomasi J. Chem. Phys. 107 1997 3032
51. J. Tomasi, B. Mennuci, and E. Cancés J. Mol. Struct. (Theochem) 464 1999 211