On the Endo/Exo Stereoselectivity of Intramolecular Diels-Alder Reactions of Hexadienylacrylates: An Interesting Failure of Density Functional Theory

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3789-3792

  Jones, Garth A ^a   Paddon Row, Michael N ^a   Sherburn, Michael S ^b   Turner, Craig I ^b  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

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ARTICLE;

EID: 0043138551     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0264713     Document Type: Article

References (29)

1. Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. Nicoloau, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668 and references therein.
2. Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. Nicoloau, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668 and references therein.
3. Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1.
4. Houk, K. N.; Beno, B. R.; Nendel, M.; Black, K.; Yoo, H. Y.; Wilsey, S. J. Mol. Struct. (THEOCHEM) 1997, 398, 169.
5. Wiest, O.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A 1997, 101, 8378.
6. Lilly, M. J.; Paddon-Row, M. N.; Sherburn, M. S.; Turner, C. I. Chem. Commun. 2000, 2213.
7. Paddon-Row, M. N.; Sherburn, M. S. Chem. Commun. 2000, 2215.
8. Turner, C. I.; Williamson, R. M.; Paddon-Row, M. N.; Sherburn, M. S. J. Org. Chem. 2001, 66, 3963.
9. Cayzer, T. N.; Wong, L. S. M.; Turner, P.; Paddon-Row, M. N.; Sberburn, M. S. Chem. Eur. J. 2002, 8, 739.
10. Tantillo, D. J.; Houk, K. N.; Jung, M. E. J. Org. Chem. 2001, 66, 1938.
11. (a) Martin, S. F.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170.
12. (b) Mori, K.; Gupta, A. K. Tetrahedron 1985, 41, 5295.
13. (c) Nugent, W. A.; Thorn, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788.
14. (d) Alexakis, A.; Jachiet, D.; Toupet, L. Tetrahedron 1989, 45, 6203.
15. (e) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840.
16. (f) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawaki, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571.
17. (g) Kim, P.; Nantz, M. H.; Kurth, M. J.; Olmstead, M. M. Org. Lett. 2000, 2, 1831.
18. (h) Jung, M. E.; Huang, A.; Johnson, T. W. Org. Lett. 2000, 2, 1835.
19. Melamede, R. Chem. Ind. (London) 2001, 724.
20. (a) Martin, S. F.; Tu, C.; Chou, T. J. Am. Chem. Soc. 1980, 102, 5274.
21. (b) Hoye, T. R.; Magee, A. S.; Trumper, W. S. Synth. Commun. 1982, 12, 183.
22. (c) Yamamoto, I.; Kohara, T.; Fujimoto, T.; Ohta., K. Phosphorus Sulfur Silicon Relat. Elem. 1996, 116, 203.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.3; Gaussian, Inc.; Pittsburgh, PA, 1998.
24. See Supporting Information for full details.
25. B3LYP TSs were characterized by carrying out harmonic frequency calculations, from which ZPEs were calculated. Frequency calculations were not carried out on the MP2-optimized TSs due to prohibitive computational overheads. Consequently, the ZPE corrections that were applied to the MP2 energies were those that were calculated at the B3LYP level.
26. Note that for system 1, there are boatlike and half-chairlike transition structures for both the 2-endo and 2-exo products. All four TSs were considered when calculating the endo:exo ratios.
27. Choi, C. H.; Kertesz, M.; Karpfen. A. J. Chem. Phys. 1997, 107, 6712.
28. Choi, C. H.; Kertesz, M.; Karpfen, A. Chem. Phys. Lett. 1997, 276, 266.
29. Note that our results suggest that BP-optimized TS geometries are adequate for single-point MP2 calculations and that it is not necessary to carry out full MP2 TS geometry optimizations.