Computational evaluation of enantioselective diels-alder reactions mediated by Corey's cationic oxazaborolidine catalysts

Journal of Organic Chemistry

Volumn 74, Issue 2, 2009, Pages 861-868

  Paddon Row, Michael N ^a   Anderson, Christopher D ^b   Houk, K N ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

B3LYP/6-31G; CARBONYL COMPLEXES; COMPUTATIONAL EVALUATIONS; COMPUTATIONAL RESULTS; DENSITY FUNCTIONAL; DIELS-ALDER REACTIONS; DIENOPHILES; ENANTIOMERIC RATIOS; ENANTIOSELECTIVE DIELS-ALDER REACTIONS; LEWIS ACIDS; OXAZABOROLIDINE; TRANSITION STATE COMPLEXES;

ACIDS; BUTADIENE; CHEMICAL REACTIONS; DENSITY FUNCTIONAL THEORY;

DYES;

1,3 BUTADIENE; CARBONYL DERIVATIVE; CATION; LEWIS ACID; OXAZABOROLIDINE DERIVATIVE; 1,3 BUTADIENE DERIVATIVE; ACROLEIN; ACRYLIC ACID DERIVATIVE; ACRYLIC ACID METHYL ESTER; BENZOQUINONE; BENZOQUINONE DERIVATIVE; BORON DERIVATIVE; DRUG DERIVATIVE; FUMARIC ACID DERIVATIVE; FUMARIC ACID DIMETHYL ESTER; FUSED HETEROCYCLIC RINGS; METHACROLEIN;

ARTICLE; CALCULATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; ENERGY YIELD; EVALUATION; PHASE TRANSITION; STEREOCHEMISTRY; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; ENZYME SPECIFICITY; STEREOISOMERISM;

ACROLEIN; ACRYLATES; BENZOQUINONES; BICYCLO COMPOUNDS, HETEROCYCLIC; BORON COMPOUNDS; BUTADIENES; COMPUTER SIMULATION; FUMARATES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 60849101360     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802323p     Document Type: Article

References (49)

1. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
2. (a) Corey, E. J. Angew. Chem. Int. Ed. 2002, 41, 1650-1667.
3. (b) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
4. (a) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992-9993.
5. (b) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808-3809.
6. (c) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388-6390.
7. (d) Ryu, D. H.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 4800-4802.
8. (a) Corey, E. J.; Rohde, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Lett. 1996, 38, 33-36.
9. (b) Corey, E. J.; Rohde, J. J. Tetrahedron Lett. 1997, 38, 37-40.
10. (c) Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Lett. 1997, 38, 4351-4354.
11. Wong, M. W. J. Ore. Chem. 2005, 70, 5487-5493.
12. Pi, Z.; Li, S. J. Phys. Chem. A 2006, 770, 9225-9230.
13. In addition, rapid exchange between Lewis acids and Lewis bases has been observed experimentally by NMR techniques. See: Farcasiu, D.; Stan, M. J. Chem. Soc., Perkin Trans. 2 1998, 1219-1222.
14. Winstein, S.; Holness, N. J. J. Am. Chem. Soc. 1955, 77, 5562-5578.
15. Pollak, P. I.; Curtin, D. Y. J. Am. Chem. Soc. 1950, 72, 961-965.
16. For a review, see: Seeman, J. I. Chem. Rev. 1983, 83, 83-134.
17. Paddon-Row, M. N.; Kwan, L. H. C.; Sherburn, M. S. Aneew. Chem., Int. Ed. 2008, 47, 7013-7017.
18. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785-789.
19. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652. For reviews of density functional methods see:
20. (c) Ziegler, T. Chem. Rev. 1991, 97, 651-667.
21. (d) Density Functional Methods in Chemistry; Labanowski, J. K., Andzelm, J. W., Eds.; Springer-Verlag: New York, 1991.
22. (e) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
23. (f) Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, 2000.
24. (a) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley &Sons, Inc.: New York, 1986.
25. (b) The Encyclopedia of Computational Chemistry; Schleyer, P. v.R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P. A., Schaefer, H. F., III, Schreiner, P. R., Eds.; John Wiley &Sons. Ltd.: Chichester, 1998.
26. (a) Wiest, O. G.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A. 1997, 101, 8378-8388.
27. (b) Kong, S.; Evanseck, J. D. J. Am. Chem. Soc. 2000, 122, 10418-10427.
28. (c) Paddon-Row, M. N.; Moran, D.; Jones, G. A.; Sherburn, M. S. J. Ore. Chem. 2005, 70, 10841-10853.
29. (d) Cayzer, T. N.; Paddon-Row, M. N.; Moran, D.; Payne, A. D.; Sherburn, M. S.; Turner, P. J. Ore. Chem. 2005, 70, 5561-5570.
30. For examples of calculations considering boron Lewis acid catalyzed DA reactions, see:
31. (a) Alves, C. N.; Carneiro, A. S.; Andrés, J.; Domingo, L. R. Tetrahedron 2006, 62, 5502-5509.
32. (b) Salvatella, L.; Ruiz-López, M. F. J. Am. Chem. Soc. 1999, 121, 10772-10780. For an example of calculations considering organic cation-catalyzed DA reactions, see:
33. (c) Sun, H.; Zhang, D. J.; Ma, C.; Liu, C. B. Int. J. Quantum Chem. 2007, 101, 1875-1885.
34. Moore, J. W.; Pearson, R. G. Kinetics and Mechanism, 3rd ed.; John Wiley &Sons Inc.: New York, 1981; Chapter 7.
35. Experimental selectivity was obtained from reactions performed at a variety of temperatures ranging from-95 to-20 °C. See ref 3.
36. (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117129.
37. (b) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245.
38. (c) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
39. (d) Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 5631-5637.
40. (e) Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
41. The solvent accessible molecular surface (using the solvent excluding surface in the PCM geometry optimizations) invariably led to failure in convergence, notwithstanding calculating the Hessian matrix at each optimization cycle.
42. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161.
43. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
44. Frisch, M. J. et al. Gaussian 03, Revision D.01; Gaussian, Inc.: Pittsburgh, PA, 2003. (22)
45. (a) Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 41274133.
46. (b) García, J. I.; Martinez-Merino, V.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1998, 120, 2415-2420.
47. (c) Garcia, J. I.; Mayoral, J. A.; Salvatella, L. Tetrahedron 1997, 53, 6057-6064.
48. Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 1870-1872.
49. Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290-8292. Also see ref 7.