Origin of stereoselectivity of the alkylation of cyclohexadienone-derived bicyclic malonates

Journal of Organic Chemistry

Volumn 78, Issue 15, 2013, Pages 7554-7564

  Volp, Kelly A ^a   Harned, Andrew M ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-C DOUBLE BONDS; COMPUTATIONAL STUDIES; DIASTEREO-SELECTIVITY; ENERGETIC DIFFERENCES; STERIC INTERACTIONS; TORSIONAL STRAIN; TOTAL SYNTHESIS; TRANSITION STATE;

ALKYLATION; KETONES;

STEREOSELECTIVITY;

2 CYCLOHEXENONE DERIVATIVE; CARBON; ELECTROPHILE; MALONIC ACID DERIVATIVE; METHYL IODIDE; NUCLEOPHILE;

ALKYLATION; ANALYTIC METHOD; ARTICLE; CHEMICAL BOND; CYCLIZATION; ENERGY; HYDROGENATION; MECHANICAL TORSION; STEREOCHEMISTRY;

EID: 84881262629     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4011238     Document Type: Article

References (67)

1. Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis, 2nd ed.; Elsevier: Amsterdam, 2012.
2. Carreira, E. M.; Kvaerno, L. Classics in Stereoselective Synthesis; Wiley-VCH: Weinheim, Germany, 2009.
3. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307
4. Ho, T.-L. Stereoselectivity in Synthesis; Wiley: New York, 1999.
5. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191
6. O'Brien, A. G. Tetrahedron 2011, 67, 9639
7. Harned, A. M.; Volp, K. A. Nat. Prod. Rep. 2011, 28, 1790
8. Bringmann, G.; Lang, G.; Mühlbacher, J.; Schaumann, K.; Steffens, S.; Rytik, P. G.; Hentschel, U.; Morschhäuser, J.; Müller, W. E. G.; Sorbicillactone, A. A Structurally Unprecedented Bioactive Novel-Type Alkaloid from a Sponge-Derived Fungus. In Sponges (Porifera); Müller, W. E. G., Ed.; Springer Verlag: Berlin, 2003; pp 231-253.
9. Bringmann, G.; Lang, G.; Gulder, T. A. M.; Tsuruta, H.; Mühlbacher, J.; Maksimenka, K.; Steffens, S.; Schaumann, K.; Stöhr, R.; Wiese, J.; Imhoff, J. F.; Perovic-Ottstadt, S.; Boreiko, O.; Müller, W. E. G. Tetrahedron 2005, 61, 7252
10. Volp, K. A.; Johnson, D. M.; Harned, A. M. Org. Lett. 2011, 13, 4486
11. Smith, A. B., III; Richmond, R. E. J. Am. Chem. Soc. 1983, 105, 575
12. Taschner, M. J.; Shahripour, A. J. Am. Chem. Soc. 1985, 107, 5570
13. Carda, M.; Marco, J. A. Tetrahedron 1992, 48, 9789
14. Bermejo, F. A.; Rico-Ferreira, R.; Bamidele-Sanni, S.; García-Granda, S. J. Org. Chem. 2001, 66, 8287
15. Maulide, N.; Markó, I. E. Chem. Commun. 2006, 1200
16. Davis, K. M.; Carpenter, B. K. J. Org. Chem. 1996, 61, 4617
17. Liu, C.; Bao, G.; Burnell, D. J. J. Chem. Soc., Perkin Trans. 1 2001, 2644
18. Jung, M. E.; Im, G.-Y. J. J. Org. Chem. 2009, 74, 8739
19. Welch, S. C.; Prakasa Rao, A. S. C.; Gibbs, C. G.; Wong, R. Y. J. Org. Chem. 1980, 45, 4077
20. Ishihara, J.; Nonaka, R.; Terasawa, Y.; Tadano, K.-i.; Ogawa, S. Tetrahedron: Asymmetry 1994, 5, 2217
21. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705
22. Tello-Aburto, R.; Kalstabakken, K. A.; Volp, K. A.; Harned, A. M. Org. Biomol. Chem. 2011, 9, 7849
23. CRC Handbook of Chemistry and Physics, 93rd ed., CRC: Boca Raton, FL; pp 15-13-15-22.
24. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
25. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
26. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
27. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
28. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
29. Johnson, E. R.; Mackie, I. D.; DiLabio, G. A. J. Phys. Org. Chem. 2009, 22, 1127
30. Steinmann, S. N.; Wodrich, M. D.; Corminboeuf, C. Theor. Chem. Acc. 2010, 127, 429
31. Zhao, Y.; Truhlar, D. G. Chem. Phys. Lett. 2011, 502, 1
32. Wheeler, S. E.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10854
33. Wheeler, S. E.; McNeil, A. J.; Müller, P.; Swager, T. M.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 3304
34. Zheng, J.; Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2009, 5, 808
35. Tang, S.-Y.; Shi, J.; Guo, Q.-X. Org. Biomol. Chem. 2012, 10, 2673
36. Caramella, P.; Rondan, N. G.; Padden-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2438
37. Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974
38. Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162
39. Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108
40. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199
41. Cherest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205
42. Seebach, D.; Maetzke, T.; Petter, W.; Klötzer, B.; Plattner, D. A. J. Am. Chem. Soc. 1991, 113, 1781
43. Inagaki, S.; Fukui, K. Chem. Lett. 1974, 509
44. Anh, N. T.; Eisenstein, O.; Lefour, J.-M.; Dau, M.-E. T. H. J. Am. Chem. Soc. 1973, 95, 6146
45. Martinelli, M. J.; Peterson, B. C.; Khau, V. V.; Hutschison, D. R.; Leanna, M. R.; Audia, J. E.; Droste, J. J.; Wu, Y.-D.; Houk, K. N. J. Org. Chem. 1994, 59, 2204
46. Lucero, M. J.; Houk, K. N. J. Org. Chem. 1998, 63, 6973
47. Cheong, P. H.-Y.; Yun, H.; Danishefsky, S. J.; Houk, K. N. Org. Lett. 2006, 8, 1513
48. Wang, H.; Kohler, P.; Overman, L. E.; Houk, K. N. J. Am. Chem. Soc. 2012, 134, 16054
49. Bur, S. K.; Martin, S. F. Org. Lett. 2000, 2, 3445
50. Carreño, M. C.; García-Cerrada, S.; Urbano, A.; Di Vitta, C. J. Org. Chem. 2000, 65, 4355
51. Tredwell, M.; Luft, J. A. R.; Schuler, M.; Tenza, K.; Houk, K. N.; Gouverneur, V. Angew. Chem., Int. Ed. 2008, 47, 357
52. Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826
53. Ando, K.; Green, N. S.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 5334
54. Meyers, A. I.; Seefeld, M. A.; Lefker, B. A. J. Org. Chem. 1996, 61, 5712 and references therein
55. Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F. J. Am. Chem. Soc. 1997, 119, 4565
56. Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F.; Williard, P. G. J. Am. Chem. Soc. 1998, 120, 7429. This was refuted by the work reported in ref 45
57. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540
58. Meyers, A. I.; Wallace, R. H. J. Org. Chem. 1989, 54, 2509
59. van der Waals radii: (H: 1.20 Å, C: 1.70 Å, O: 1.52 Å). See: Bondi, A. J. Phys. Chem. 1964, 68, 441
60. Maria, P.-C.; Gal, J.-F. J. Phys. Chem. 1985, 89, 1296
61. Gal, J.-F.; Maria, P.-C.; Massi, L.; Mayeux, C.; Burk, P.; Tammiku-Taul, J. Int. J. Mass Spectrom. 2007, 267, 7
62. Laurence, C.; Gal, J.-F. Lewis Basicity and Affintiy Scale. Data and Measurement; Wiley: West Sussex, U.K., 2010; pp 323-399.
63. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378
64. For a discussion on strengths and limitations associated with solvent models, see: Cramer, C. J. Essentials of Computational Chemistry: Theories and Models, 2nd ed.; Wiley: West Sussex, U.K., 2004; pp 385-427.
65. Wang, H.; Michalak, K.; Michalak, M.; Jinénez-Osés, G.; Wicha, J.; Houk, K. N. J. Org. Chem. 2010, 75, 762
66. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.;; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2010.
67. Wheeler, S. E.; Houk, K. N. J. Chem. Theory Comput. 2010, 6, 395