Torsional control of epoxidation stereoselectivity in 1,2-dihydronaphthalenes. Transition state modeling with semiempirical quantum mechanics

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 6973-6977

  Lucero, Melissa J ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000768745     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980760g     Document Type: Article

References (16)

1. Linker, T.; Peters, K.; Peters, E.-M.; Rebien, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2487.
2. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
3. Detailed structural data may be obtained from Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, Germany (Depository number CSD-405437).
4. Rabideau, P. W.; Sygula, A. The Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Heteroaromatic Compounds; VCH: Weinheim, 1989; pp 77-81.
5. Corey, E. J.; Sneen, R. A. J. Am. Chem. Soc. 1956, 78, 6269.
6. ToromanofT, E. Tetrahedron 1980, 78, 6269.
7. Vedjes, E.; Dent, W. H., Ill; Kendall, J. T.; Oliver, P. A. J. Am. Chem. Soc. 1996,118, 3556.
8. Ducrot, P.; Bucourt, R.; Thal, C.; Marçot, B.; Mayrargue, J.; Moskowitz, H. Tetrahedron 1996, 52, 6699.
9. (a) Rondan, N. G.; Paddon-Row: M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982,104, 4974.
10. (b) Paddon-Row: M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162.
11. 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.
12. 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.
13. SPARTAN version 4.0: Wavefunction, Inc., 18401 Von Karman Ave., #370, Irvine, ÇA 92715, 1995.
14. Gaussian 94, Revision D.3: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
15. Eksterowicz, J. E.; Houk K. N. Chem. Rev. 1993, 93, 2439.
16. Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147.