Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates

Journal of the American Chemical Society

Volumn 130, Issue 12, 2008, Pages 3740-3741

  Li, Guotao ^a   Zhang, Guozhu ^a   Zhang, Liming ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CARBOXYLIC ACID DERIVATIVE; GOLD;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

ALKADIENES; ALKYNES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOGOLD COMPOUNDS; PENTANOIC ACIDS; STEREOISOMERISM;

EID: 41149133831     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800001h     Document Type: Article

References (23)

1. For recent reviews on gold catalysis, see: (a) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271-2296.
2. (B) Fürstner, A.; Davis, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449.
3. (c) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211.
4. For a review on Au-catalyzed reactions of propargylic esters, see (d) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750-2752.
5. (a) Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804-16805.
6. (b) Yu, M.; Li, G.; Wang, S.; Zhang, L. Adv. Synth. Catal. 2007, 349, 871-875.
7. (c) Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414-8415.
8. (d) Buzas, A.; Gagosz, F. J. Am. Chem. Soc. 2006, 128, 12614-12615.
9. (e) Marion, N.; Diez-Gonzalez, S.; de Fremont, P.; Noble, A. R.; Nolan, S. P. Angew. Chem., Int. Ed. 2006, 45, 3647-3650.
10. For selected examples, see: (a) Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505-8513.
11. (b) Mamane, V.; Gress, T.; Krause, H.; Füstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655.
12. (c) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802-5803.
13. (d) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002-18003.
14. (e) Amijs, C. H. M.; Lopez-Carrillo, V.; Echavarren, A. M. Org. Lett. 2007, 9, 4021-4024.
15. A recent calculation suggests that double 1,2-acyloxy migrations can also account for the 3,3-rearrangement and all these transformations are reversible. For reference, see: Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 613.
16. For a study with Pt(II) as catalyst, see: Hardin, A. R.; Sarpong, R. Org. Lett. 2007, 9, 4547-4550.
17. For related Cu and Pt catalysis, see: (a) Prasad, B. A. B.; Yoshimoto, F. K.; Sarpong, R. J. Am. Chem. Soc. 2005, 127, 12468-12469.
18. (b) Schwier, T.; Sromek, A. W.; Yap, D. M. L.; Chernyak, D.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 9868-9878.
19. For other Au-catalyzed diene formations, see: (a) Wang, S. Z.; Zhang, L. M. Org. Lett. 2006, 8, 4585-4587.
20. (b) Buzas, A. K.; Istrate, F. M.; Gagosz, F. Org. Lett. 2007, 9, 985-988.
21. (a) Li, G.; Zhang, L. Angew. Chem., Int. Ed. 2007, 46, 5156-5159.
22. (b) Ricard, L.; Gagosz, F. Organometallics 2007, 26, 4704-4707.
23. Nevado, C.; Echavarren, A. M. Chem.-Eur. J. 2005, 11, 3155-3164.