Crossed intermolecular [2+2] cycloadditions of acyclic enones via visible light photocatalysis

Journal of the American Chemical Society

Volumn 131, Issue 41, 2009, Pages 14604-14605

  Du, Juana ^a   Yoon, Tehshik P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC ENONES; CYCLOADDITIONS; CYCLOBUTANES; DIASTEREOSELECTIVITIES; DIVERSE RANGE; GOOD YIELD; UNSYMMETRICAL; UV PHOTOLYSIS; VISIBLE LIGHT; VISIBLE-LIGHT IRRADIATION; VISIBLE-LIGHT PHOTOCATALYSIS;

BUTANE; LIGHT SOURCES; PHOTOCATALYSIS; PHOTOLYSIS; RUTHENIUM;

LIGHT;

ARYL ENONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIMERIZATION; ISOLATION PROCEDURE; ISOMERIZATION; LIGHT; PHOTOCATALYSIS; PHOTOCHEMISTRY; SUNLIGHT; ULTRAVIOLET IRRADIATION;

ALKENES; CATALYSIS; KETONES; LIGHT; PHOTOCHEMICAL PROCESSES;

EID: 70350064068     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903732v     Document Type: Article

References (17)

1. Ciamician, G.; Silber, P. Chem. Ber. 1908, 41, 1928-1935.
2. (a) For recent reviews of [2+2] enone photocycloadditions, see: Baldwin, S. W. In Organic Photochemistry; Padwa, A., Ed; Marcel Dekker: New York, 1981; Vol.5, pp 123-225.
3. (b) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473.
4. (c) Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3-22.
5. (d) Bach, T. Synthesis 1998, 683-703.
6. (e) Iriondo-Alberdi, J.; Greaney, M. F. Eur. J. Org. Chem. 2007, 4801-4815.
7. (f) Hoffmann, N. Chem. Rev. 2008, 108, 1052-1103.
8. Morrison, H.; Rodriguez, O. J. Photochem. 1974, 3, 471-474.
9. For reviews of transition metal mediated photocatalysis in organic synthesis, see: (a) Salomon, R. G. Tetrahedron 1983, 39, 485-575.
10. (b) Hennig, H. Coord. Chem. Rev. 1999, 182, 101-123.
11. Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886-12887.
12. (a) Baik, T.-G.; Luis, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 6716-6717.
13. (b) Wang, L.-C.; Jang, H.-Y.; Roh, Y.; Lynch, V.; Schultz, A. J.; Wang, X.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448-9453.
14. (c) Roh, Y.; Jang, H.-Y.; Lynch, V.; Bauld, N. L.; Krische, M. J. Org. Lett. 2002, 4, 611-613.
15. (d) Yang, J.; Cauble, D. F.; Berro, A. J.; Bauld, N. L.; Krische, M. J. J. Org. Chem. 2004, 69, 7979-7984.
16. (e) Yang, J.; Felton, G. A. N.; Bauld, N. L.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 1634-1635.
17. 2NEt are not consumed in the reaction, highly diastereoselective cycloaddition is only observed when these additives are present in excess. The reason for this dependence is not clear at this time and is the subject of ongoing investigation in our lab.