Rhodium(I)-catalyzed [4+2+2] cycloadditions of 1,3-dienes, alkenes, and alkynes for the synthesis of cyclooctadienes

Journal of the American Chemical Society

Volumn 128, Issue 16, 2006, Pages 5354-5355

  Wender, Paul A ^a   Christy, Justin P ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; ALKYNE; CYCLOALKENE; CYCLOOCTADIENE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CYCLOADDITION; DIASTEREOISOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33646442650     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060878b     Document Type: Article

References (18)

1. Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434.
2. (a) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966.
3. (b) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154.
4. Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
5. For examples of [4+2+1] and [2+2+1] reactions with diene-ynes, see: (a) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem., Int. Ed. 2003, 42, 1853-1857.
6. For examples of [2+2+1] reactions with diene-enes, see: (b) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948-5949.
7. For an impressive alternative [4+2+1] cycloaddition, see: (c) Ni, Y.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 2609-2614 and references therein.
8. Gilbertson, S.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784-8785.
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10. J. Am. Chem. Soc. 2002, 124, 8782-8783.
11. (b) Evans, P. A.; Baum, E. W. J. Am. Chem. Soc. 2004, 126, 11150-11151.
12. (c) Evans, P. A.; Baum, E. W.; Fazal, E. W.; Aleem, N.; Pink, M. Chem. Commun. 2005, 1, 63-65.
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14. For other examples of related metal-catalyzed [4+2+2] cycloadditions, see: (a) Chen, Y.; Kiattansakul, R.; Ma, B.; Synder, J. K. J. Org. Chem. 2001, 66, 6932-6942.
15. (b) Ma, B.; Snyder, J. K. Organometallics 2002, 21, 4688-4695.
16. (c) Varela, J.; Castedo, L.; Saa, C. Org. Lett. 2003, 5, 2841-2844.
17. (d) Murakami, M.; Ashida, S.; Matsuda, T. J. Am. Chem. Soc. 2006, 128, 2166-2167.
18. For a review of related rhodium-catalyzed cycloadditions, see: Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VHC Verlag GmbH & Co.: Weinheim, Germany, 2005.