The ionic Diels-Alder reaction of the allyl cation and butadiene: Theoretical investigation of the mechanism

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1759-1762

  De Pascual Teresa, Beatriz ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY;

BETULACEAE;

EID: 0029887901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00170-0     Document Type: Article

References (17)

1. Carruthers, W. "Cycloaddition Reactions in Organic Synthesis" 1990, Pergamon Press, Oxford.
2. Hoffmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1973, 12, 819.
3. (a) Sauer, J. and Sustmann, R. Angew. Chem. Int. Ed. Engl. 1980, 19, 779.
4. (b) Houk, K. N.; Gonzalez, J. and Li, Y. Acc. Chem. Res. 1995, 28, 81 and references therein.
5. Woodward, R. B and Hoffmann, R. "The Conservation of Orbital Symmetry" 1970, Academic press, New York.
6. Hoffmann, H. M. R. Angew. Chem. Internat. Ed. Engl. 1984, 23, 1.
7. Haynes, R. K.; King, G. R. and Vonwiller, S. C. J. Org. Chem. 1994, 59, 4743.
8. (a) Gassman, P. G. and Singleton, D. A. J. Am. Chem. Soc. 1984, 106, 6085.
9. (b) Gassman, P. G. and Singleton, D. A. J. Org. Chem. 1986, 51, 3076.
10. (c) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J. and Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182.
11. (d) Gassman, P. G. and Gorman, D. B. J. Am. Chem. Soc. 1990, 112, 8623.
12. Gassman, P. G. and Gorman, B. D. J. Am .Chem. Soc. 1990, 112, 8624.
13. Gorman, B. D. and Gassman, P. G. J. Org. Chem. 1995, 60, 977.
14. GAUSSIAN 92. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M. ; Gill, P. M. V.; Wong, M. W. ; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P. and Pople, J. A. Gaussian, Inc. Pittsburgh, PA
15. Houk, K. N.; Li, Y. and Evanseck, J. D. Angew. Chem. Int. Ed. Engl. 1992, 31, 682.
16. 13
17. Cramer, C. J. and Barrows, S.E. J. Org. Chem. 1994, 59 , 7591.