Enantioselective Photochemical Synthesis of a Simple Alkene via the Solid State Ionic Chiral Auxiliary Approach

Journal of Organic Chemistry

Volumn 69, Issue 8, 2004, Pages 2711-2718

  Chen, Shuang ^a   Patrick, Brian O ^a   Scheffer, John R ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; DERIVATIVES; PHOTOCHEMICAL REACTIONS; SINGLE CRYSTALS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CLEAVAGE PROCESSES; REACTANTS;

OLEFINS;

3A,4,5,6,7,7A HEXAHYDRO 1H INDENE; ACETOPHENONE DERIVATIVE; ALKENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; INDENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; PHOTOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 1842689092     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0358271     Document Type: Article

References (25)

1. Partial kinetic resolution of unfunctionalized simple olefins has been reported. For references on kinetic resolution of axially dissymmetric cyclic alkenes by asymmetric dihydoxylation, see: Hoveyda, A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 489 and references therein. For references on kinetic resolution of terminal alkenes by alkene polymerization with chiral zirconocene catalysts, see: Bercaw, J. E.; Min, E. Y.-J.; Levy, C. J.; Baar, C. R. Polym. Mater. Sci. Eng. 2002, 87, 62 and references therein.
2. Partial kinetic resolution of unfunctionalized simple olefins has been reported. For references on kinetic resolution of axially dissymmetric cyclic alkenes by asymmetric dihydoxylation, see: Hoveyda, A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 489 and references therein. For references on kinetic resolution of terminal alkenes by alkene polymerization with chiral zirconocene catalysts, see: Bercaw, J. E.; Min, E. Y.-J.; Levy, C. J.; Baar, C. R. Polym. Mater. Sci. Eng. 2002, 87, 62 and references therein.
3. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754.
4. Goldberg, S. I.; Lam, F.-L. J. Am. Chem. Soc. 1969, 91, 5113.
5. Cope, A. C.; Funke, W. R.; Jones, F. N. J. Am. Chem. Soc. 1966, 88, 4693.
6. Imboden, C.; Villar, F.; Renaud, P. Org. Lett. 1999, 1, 873.
7. (a) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203.
8. (b) Scheffer, J. R. Can. J. Chem. 2001, 79, 349.
9. For general reviews of the Norrish/Yang type II reaction, see: (a) Wagner, P.; Park, B.-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, Chapter 4.
10. (b) Wagner, P. J. In Molecular Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Chapter 20.
11. (c) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168.
12. Ariel, S.; Ramamurthy, V.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1983, 105, 6959.
13. Ariel, S.; Evans, S. V.; Garcia-Garibay, M.; Harkness, B. R.; Omkaram, N.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1988, 110, 5591.
14. Wagner, P. J. In CRC Handbook of Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: Boca Raton, FL, 1995; Chapter 38.
15. Cheung, E.; Netherton, M. R.; Scheffer, J. R.; Trotter, J. Org. Lett. 2000, 2, 77.
16. Wagner, P. J.; Kelso, P. A.; Kempainen, A. E. J. Am. Chem. Soc. 1968, 90, 5896.
17. Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647.
18. Scaiano, J. C.; Lissi, E. A.; Encina, M. V. Rev. Chem. Intermed. 1978, 2, 139. Also see refs 7b, 7c, and 9.
19. Engler, E. M.; Andose, J. D.; Schleyer, P. v. R. J. Am. Chem. Soc. 1973, 95, 8005.
20. Cox, J. D.; Pilcher, G. In Thermochemistry of Organic and Organometallic Compounds; Academic Press: London, UK, 1970; pp 166, 571, 579, 580, and 590.
21. Fujisaki, N.; Ruf, A.; Gaumann, T. J. Am. Chem. Soc. 1985, 107, 1605.
22. Using the solid-state ionic chiral auxiliary approach, high ee values have been obtained in the Norrish type II cleavage reaction with the alkene product being a solid: Chong, K. C. W.; Scheffer, J. R. J. Am. Chem. Soc. 2003, 125, 4040.
23. Turecek, F.; Vystrcil, A. Collect. Czech. Chem. Commun. 1976, 41, 1571.
24. Stierman, T. J.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 3971.
25. Smissman, E. E.; Li, J. P.; Israili, Z. H. J. Org. Chem. 1968, 33, 4231.