Diastereo- and regioselective Diels-Alder reactions of 2-phosphaindolizines

Tetrahedron

Volumn 64, Issue 27, 2008, Pages 6395-6401

  Bansal, Raj K ^a   Gupta, Neelima ^a   Kumawat, Surendra K ^a   Dixit, Govind ^a  

^a UNIVERSITY OF RAJASTHAN   (India)

Author keywords

2 Phosphaindolizines; DFT calculations; Diels Alder reactions; Regioselectivity

Indexed keywords

1,3 BUTADIENE; 2 PHOSPHAINDOLIZINE DERIVATIVE; 2,3 DIMETHYLBUTADIENE; 3 ETHOXYCARBONYL 1 METHYL 2 PHOSPHAINDOLIZINE; INDOLIZINE DERIVATIVE; ISOPRENE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

ALNUS;

EID: 44349130272     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.080     Document Type: Article

References (62)

1. Carruthers W. Cycloaddition Reactions in Organic Synthesis (1990), Pergamon, Oxford, UK
2. Winkler J.D. Chem. Rev. 96 (1996) 167
3. Dell C.P. J. Chem. Soc., Perkin Trans. 1 (1998) 3873
4. Nicolaou K.C., Snyder S.A., Montagnon T., and Vassilikogiannakis G. Angew. Chem., Int. Ed. 41 (2002) 1668
5. Dillon K.B., Mathey F., and Nixon J.F. Phosphorus: the Carbon Copy (1988), Wiley, New York, NY
6. Mathey F. Acc. Chem. Res. 25 (1992) 90
7. Schmidpeter A. Heteroat. Chem. 10 (1999) 529
8. Schmidt M.W., Truong P.N., and Gordon M.S. J. Am. Chem. Soc. 109 (1987) 5217
9. Schleyer P.v.R., and Kost D. J. Am. Chem. Soc. 110 (1988) 2105
10. Nyulaszi L., Veszprémi T., and Réffy J. J. Phys. Chem. 97 (1993) 4011
11. Le Floch P. Coord. Chem. Rev. 250 (2006) 267
12. Markovskii L.N., and Romanenko V.D. Tetrahedron 45 (1989) 6019
13. Appel R. In: Regitz M., and Scherer O.J. (Eds). Multiple Bonds and Low Coordination in Phosphorus Chemistry (1990), Thieme, Stuttgart 157
14. Schmidpeter A., and Karaghiosoff K. In: Regitz M., and Scherer O.J. (Eds). Multiple Bonds and Low Coordination in Phosphorus Chemistry (1990), Thieme, Stuttgart 258
15. Schmidpeter A. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry-II Vol. 3 (1996), Pergamon, Oxford 709 715; Vol. 4, p 771
16. Schmidpeter A. In: Mathey F. (Ed). Phosphorus-Carbon Heterocyclic Chemistry: the Rise of a New Domain (2001), Elsevier, Oxford 363
17. Bansal R.K., Gupta N., and Gupta N. Heteroat. Chem. 15 (2004) 271
18. Bansal R.K., Karaghiosoff K., and Schmidpeter A. Tetrahedron 50 (1994) 7675
19. Bansal R.K., and Heinicke J. Chem. Rev. 101 (2001) 3549
20. Bansal R.K., Gupta N., and Kumawat S.K. Curr. Org. Chem. 11 (2007) 33
21. Quin L.D. The Heterocyclic Chemistry of Phosphorus (1981), Wiley-Interscience, New York, NY pp 141, 390
22. Märkl G. Methoden der Organischen Chemie (Houben-Weyl) Vol. E1 (1982), Thieme, Stuttgart pp 72
23. Märkl G. In: Regitz R., and Scherer O.J. (Eds). Multiple Bonds and Low Coordination in Phosphorus Chemistry (1990), Thieme, Stuttgart 220
24. Mathey F. Coord. Chem. Rev. 137 (1994) 1
25. Avarvari N., Le Floch P., Ricard L., and Mathey F. Organometallics 16 (1997) 4089
26. Sava X., Mézailles N., Maigrot N., Nief F., Ricard L., Mathey F., and Le Floch P. Organometallics 18 (1999) 4205
27. Rhörig U., Mézailles N., Maigrot N., Ricard L., Mathey F., and Le Floch P. Eur. J. Inorg. Chem. (2000) 2565
28. Welfelé S., Mézailles N., Maigrot N., Ricard L., Mathey F., and Le Floch P. New J. Chem. 25 (2001) 1264
29. Avarvari N., Maigrot N., Ricard L., Mathey F., and Le Floch P. Chem.-Eur. J. 5 (1999) 2109
30. Bansal R.K., Karaghiosoff K., Gupta N., Schmidpeter A., and Spindler C. Chem. Ber. 124 (1991) 475
31. Bansal R.K., Kabra V., and Gupta N. Indian J. Chem. 31B (1992) 254
32. Gupta N., Jain C.B., Heinicke J., Bharatiya N., Bansal R.K., and Jones P.G. Heteroat. Chem. 9 (1998) 333
33. Bansal R.K., Surana A., and Gupta N. Tetrahedron Lett. 40 (1999) 1565
34. Bansal R.K., Gupta N., Baweja M., Hemrajani L., and Jain V.K. Heteroat. Chem. 12 (2001) 602
35. Hudson H.R., Dillon K.B., and Walker B.J. In: Tebby J.C. (Ed). CRC Handbook of Phosphorus-31 Nuclear Magnetic Resonance DATA (1991), CRC, Boca Raton, FL 181
36. Bansal R.K., Jain V.K., Gupta N., Gupta N., Hemrajani L., Baweja M., and Jones P.G. Tetrahedron 58 (2002) 1573
37. 31P NMR Spectroskopie Vol. 3 (1993), Thieme, Stuttgart pp 135
38. Bansal R.K., Karaghiosoff K., Gupta N., Gandhi N., and Kumawat S.K. Tetrahedron 61 (2005) 10521
39. Bansal R.K., Gupta N., and Kumawat S.K. Z. Naturforsch. 63B (2008) 321
40. Alcaraz J., and Mathey F. J. Chem. Soc., Chem. Commun. (1984) 508
41. Bansal R.K., Gupta N., and Kumawat S.K. Tetrahedron 62 (2006) 1548
42. Bansal R.K., Gupta N., Kumawat S.K., and Gupta R. Heteroat. Chem. 17 (2006) 402
43. Bansal R.K., Karaghiosoff K., Gupta N., Kabra V., Mahnot R., Sharma D.C., Munjal R., and Kumawat S.K. Z. Naturforsch. 60B (2005) 7
44. Glendening E.D., Reed A.E., Carpenter J.E., and Weinhold F. NBO, version 3.1 (1996), Theoretical Chemistry Institute, University of Wisconsin, Madison, WI
45. Pellegrinet S.C., Silva M.A., and Goodman J.M. J. Am. Chem. Soc. 123 (2001) 8832
46. Domingo L.R., Arnó M., and Andrés J. J. Org. Chem. 64 (1999) 5867
47. Margetic D., Johnston M.R., and Warrener R.N. Molecules 5 (2001) 1417
48. Domingo L.R., Oliva M., and Andrés J. J. Org. Chem. 66 (2001) 6151
49. Domingo L.R., and Aurell M.J. J. Org. Chem. 67 (2002) 959
50. Domingo L.R. Tetrahedron 58 (2002) 3765
51. Domingo L.R., Aurell M.J., Pérez P., and Contreras R. J. Phys. Chem. A 106 (2002) 6871
52. Silva M.A., Pellegrinet S.C., and Goodman J.M. J. Org. Chem. 68 (2003) 4059
53. Silva M.A., Pellegrinet S.C., and Goodman J.M. ARKIVOC (2003) 556
54. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., 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., and Pople J.A. Gaussian 03, Revision B.05 (2003), Gaussian, Pittsburgh, PA
55. Gonzalez C., and Schlegel H.B. J. Phys. Chem. 94 (1990) 5523
56. Wiberg K.B. Tetrahedron 24 (1968) 1083
57. Tomasi J., and Persico M. Chem. Rev. 94 (1994) 2027
58. Simkin B.Y., and Sheikhet I. Quantum Chemical and Statistical Theory of Solutions-a Computational Approach (1995), Ellis Horwood, London
59. Cancés M.T., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032
60. Mennucci B., and Tomasi J. J. Chem. Phys. 106 (1997) 5151
61. Mennucci B., Cancés E., and Tomasi J. J. Phys. Chem. B 101 (1997) 10506
62. Tomasi J., Mennucci B., and Cancés E. J. Mol. Struct. (THEOCHEM.) 464 (1999) 211