Origins of stereoselectivities of dihydroxylations of cis -bicyclo[3.3.0]octenes

Journal of the American Chemical Society

Volumn 134, Issue 38, 2012, Pages 16054-16058

  Wang, Hao ^a   Kohler, Philipp ^b   Overman, Larry E ^b   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL STUDIES; CONFORMATIONAL RIGIDITY; CYCLOPENTENES; OCTENES; STERIC EFFECT; TORSIONAL EFFECT; TOTAL SYNTHESIS;

RIGIDITY; SYNTHESIS (CHEMICAL);

STEREOSELECTIVITY;

2 OCTENE; BICYCLO[3.3.0]OCTENE; CHROMODOROLIDE A; CYCLOPENTENE DERIVATIVE; DITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; DIHYDROXYLATION; STATIC ELECTRICITY; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; TORSION;

BICYCLO COMPOUNDS; HYDROXYLATION; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 84866675215     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3075538     Document Type: Article

References (33)

1. Dumdei, E. J.; de Silva, E. D.; Andersen, R. J.; Choudhary, M. I.; Clardy, J. J. Am. Chem. Soc. 1989, 111, 2712-2713
2. Morris, S. A.; de Silva, E. D.; Andersen, R. J. Can. J. Chem. 1991, 69, 768-771
3. Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547
4. Ruano, J. L.; Núñez, A., Jr.; Martín; Fraile, A. J. Org. Chem. 2008, 73, 9366-9371
5. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544
6. De March, P.; Font, J.; Gracia, A.; Qingying, Z. J. Org. Chem. 1995, 60, 1814-1822
7. Rout, L.; Harned, A. M. Chem.-Eur. J. 2009, 15, 12926-12928
8. Fariña, F.; Martín, M. R.; Martín, M. V. An. Quim. 1979, 75, 144-149
9. VanRheenen, V; Kelly, R. C.; Cha, R. C. Tetrahedron Lett. 1976, 17, 1973-1976
10. Frisch, M. J. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2010.
11. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
12. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, 37, 785-789
13. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310
14. For dispersion correction, see
15. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
16. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104
17. McMullin, C. L.; Jover, J.; Harvey, J. N.; Fey, N. Dalton Trans. 2010, 39, 10833-10836
18. Antoline, J. E.; Krenske, E. H.; Lohse, A. G.; Houk, K. N.; Hsung, R. P. J. Am. Chem. Soc. 2011, 133, 14443-14451
19. Caramella, P.; Rondan, N. G.; Paddon, M. N.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2438-2440
20. Rondan, N. G.; Paddon, M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974-4976
21. Paddon, M. N.; Rondan, N. G; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166
22. Lucero, M. J.; Houk, K. N. J. Org. Chem. 1998, 63, 6973-6977
23. Cheong, P. H.; Yun, H.; Danishefsky, S. J.; Houk, K. N. Org. Lett. 2006, 8, 1513-1516
24. Martinelli, M. J.; Peterson, B. C.; Khau, V. V.; Hutchison, D. R.; Leanna, M. R.; Audia, J. E.; Droste, J. J.; Wu, Y.-D.; Houk, K. N. J. Org. Chem. 1994, 59, 2204-2210
25. Houk, K. N.; Paddon, 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, 1108-1117
26. Broom, N.; OHanlon, P. G.; Simpson, T. J.; Stephen, R.; Willis, C. L. J. Chem. Soc., Perkin Trans. 1 1995, 3067-3072
27. Fretmanlis, J.; Gerca, L.; Turovskis, I.; Liepins, E.; Lola, D.; Mishnev, A.; Bundule, M.; Bleidelis, J. J. Prakt. Chem. 1987, 329, 39-48
28. Leonard, J.; Hussain, N. J. Chem. Soc., Perkin Trans. 1 1994, 49-60
29. Neufellner, E.; Kapeller, H.; Griengl, H. Tetrahedron 1998, 54, 11043-11062
30. Ernst, M.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 4054-4056
31. Marschner, C.; Baumgartner, J.; Griengl, H. J. Org. Chem. 1995, 60, 5224-5235
32. Choudhary, A.; Gandla, D.; Krow, G. R.; Raines, R. T. J. Am. Chem. Soc. 2009, 131, 7244-7246
33. Jakobsche, C. E.; Choudhary, A.; Miller, S. J.; Raines, R. T. J. Am. Chem. Soc. 2010, 132, 6651-6653