Origins of the regioselectivities in the Diels-Alder reactions of vinylindenes with 1,4-quinone monoketal and acrolein dienophiles

Journal of Organic Chemistry

Volumn 74, Issue 17, 2009, Pages 6770-6776

  Hayden, Amy E ^a   DeChancie, Jason ^a   George, Alexander H ^a   Dai, Mingji ^b   Yu, Maolin ^b   Danishefsky, Samuel J ^b,c   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

B3LYP/6-31G; CHEMICAL EQUATIONS; DIELS-ALDER REACTION; DIENOPHILES; ELECTROSTATIC MODELS; FRONTIER MOLECULAR ORBITALS; LEWIS ACID CATALYSTS; REGIOCHEMICAL; STERIC CONTROL;

ALDEHYDES; CHEMICAL REACTIONS; HERBICIDES; MOLECULAR ORBITALS; OLEFINS;

DENSITY FUNCTIONAL THEORY;

ACETAL DERIVATIVE; ACROLEIN DERIVATIVE; FLUORENONE DERIVATIVE; FLUOSTATIN C; LEWIS ACID; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

ACIDS; ACROLEIN; CATALYSIS; CHEMISTRY, ORGANIC; FLUORENES; INDENES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; QUINONES; STATIC ELECTRICITY; THERMODYNAMICS; VINYL COMPOUNDS;

EID: 69549128359     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901473h     Document Type: Article

References (26)

1. Yu, M.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 2783-2785.
2. Breuning, M.; Corey, E. J. Org. Lett. 2001, 3, 1559-1562.
3. Teo, Y.-C.; Loh, T.-P. Org. Lett. 2005, 7, 2539-2541.
4. Stork, G.; Wagle, S. S.; Mukharji, P. C. J. Am. Chem. Soc. 1953, 75, 3197-3204.
5. Nazarov, I. N.; Ananchenko, S. N.; Torgov, I. V. Russ. Chem. B 1957, 8, 84-90.
6. Bergmann, E. D.; Becker, A. J. Am. Chem. Soc. 1959, 81, 221-225.
7. (a) Orsini, F.; Pelizzoni, F.; Pitea, F.; Abbondanti, E.; Mugnoli, A. J. Org. Chem. 1983, 48, 2866-2870.
8. (b) Pitea, F.; Gastaldi, M.; Orsini, F.; Pelizzoni, F.; Mugnoli, A.; Abbondanti, E. J. Org. Chem. 1985, 50, 1853-1859.
9. Stojanac, Z.; Dickinson, R. A.; Stojanac, N.; Woznow, R. J.; Valenta, Z. Can. J. Chem. 1975, 53, 616-618.
10. Trost, B. M.; Ippen, J.; Vladuchick, W. C. J. Am. Chem. Soc. 1977, 99, 8116-8118.
11. Hendrickson, J. B.; Singh, V. J. Chem. Soc., Chem. Commun. 1983, 837-838.
12. Guner, O. F.; Ottenbrite, R. M.; Shillady, D. D.; Alston, P. V. J. Org. Chem. 1987, 52, 391-394.
13. Mander, L. N.; MacLachlan, M. M. J. Am. Chem. Soc. 2003, 125, 2400-2401.
14. O'Conner, P. D.; Mander, L. N.; MacLachlan, M. M. W. Org. Lett. 1994, 5, 703-706.
15. Çelebi-ØOlçüm, N.; Ess, D. H.; Aviyente, V.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 4528-4529.
16. (a) Houk, K. N. J. Am. Chem. Soc. 1973, 95, 4092-4094.
17. (b) Houk, K. N.; Strozier, R. W. J. Am. Chem. Soc. 1973, 95, 4094-4096.
18. (c) Houk, K. N. Acc. Chem. Res. 1975, 8, 361-369.
19. (a) Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381-7396.
20. (b) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663-666.
21. (c) Arteca, G. A.; Jammal, V. B.; Mezey, P. G. J. Comput. Chem. 1988, 9, 608-619.
22. (d) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625-4633.
23. (a) Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol.2, pp 181-271.
24. (b) An excellent example of the dominance of a 1-substituent (methyl) over a 2-substituent (trimethylsiloxy) can be found in a coriolin synthesis: Danishefsky, S.; Zamboni, R.; Kahn, M.; Etheredge, S. J. J. Am. Chem. Soc. 1980, 102, 2097-2098.
25. Frisch, M. J. et al. Gaussian03, Revision C.02; Gaussian, Inc., Wallingford, CT, 2004.
26. Wheeler, S. E.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10854-10855.