Platinum(II)-catalyzed generation and [3+2] cycloaddition reaction of α,β-unsaturated carbene complex intermediates for the preparation of polycyclic compounds

Journal of the American Chemical Society

Volumn 133, Issue 4, 2011, Pages 689-691

  Saito, Kodai ^a   Sogou, Hideyuki ^a   Suga, Takuya ^a   Kusama, Hiroyuki ^a   Iwasawa, Nobuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURANS; CARBENE COMPLEXES; CYCLOADDITION REACTION; ELECTROPHILIC ACTIVATION; FIVE-MEMBERED RINGS; HIGH YIELD; IN-SITU; POLYCYCLIC COMPOUNDS; PROPARGYL ETHERS; VINYL ETHERS;

ACETYLENE; CATALYSIS; CYCLOADDITION; ETHERS; PLATINUM; REACTION INTERMEDIATES; UNSATURATED COMPOUNDS;

PLATINUM COMPOUNDS;

BENZOFURAN DERIVATIVE; CARBENE; INDOLE DERIVATIVE; NAPHTHOL DERIVATIVE; PLATINUM; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLOADDITION;

EID: 79851499669     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja108586d     Document Type: Article

References (32)

1. For recent reviews, see: (a) Fiirstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449.
2. (b) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350.
3. (c) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271-2296.
4. (d) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208-3221.
5. (e) Shen, H. C. Tetrahedron 2008, 64, 7847-7870.
6. For recent reviews of transition metal-catalyzed 1, 2-acyloxy migration, see: (a) Marco-Contelles, J.; Soriano, E. Chem. Eur. J. 2007, 13, 1350-1357.
7. (b) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750-2752.
8. (c) Marion, N.; Lemière, G.; Correa, A.; Costabile, C.; Ramón, R. S.; Moreau, X.; Frémont, P.; Dahmane, R.; Hours, A.; Lesage, D.; Tabet, J.-C.; Goddard, J.-P.; Gandon, V.; Cavallo, L.; Fensterbank, L.; Malacria, M.; Nolan, S. P. Chem. Eur. J. 2009, 15, 3243-3260.
9. (a) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260-11261.
10. (b) Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 12598-12599.
11. (c) Peng, L.; Zhang, X.; Zhang, S.; Wang, J. J. Org. Chem. 2007, 72, 1192-1197.
12. (d) Sanz, R.; Miguel, D.; Gohain, M.; García-García, P.; Fernández-Rodríguez, M. A.; González-Pérez, A.; Nieto-Faza, O.; De Lera, Á. R.; Rodríguez, F. Chem. Eur. J. 2010, 16, 9818-9828. See also
13. (e) Lin, G.-Y.; Li, C.-W.; Hung, S.-H.; Liu, R.-S. Org. Lett. 2008, 10, 5059-5062.
14. For examples of cyclopropanation reaction by using unsaturated carbene complexes generated from 1, 2-acyloxy migration of propargyl esters, see: (a) Rautenstrauch, V. J. Org. Chem. 1984, 49, 950-952.
15. (b) Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505-8513.
16. (c) Mainetti, E.; Mouriès, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem. Int. Ed. 2002, 41, 2132-2135.
17. (d) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002-18003.
18. For other cycloaddition reactions, see: (a) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244-9245.
19. (b) Shapiro, N. D.; Shi, Y.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 11654-11655.
20. (c) Zheng, H.; Zheng, J.; Yu, B.; Chen, Q.; Wang, X.; He, Y.; Yang, Z.; She, X. J. Am. Chem. Soc. 2010, 132, 1788-1789.
21. One specific example of the [3+2] cycloaddition reaction with an electron-rich olefin, N-benzylindole, of α, β-unsaturated carbene complexes generated catalytically from a propargyl ketal using Au (I) catalyst was reported. See ref 3b.
22. Recently, [3+2] cycloaddition reaction with electron-deficient alkynes of α, β-unsaturated carbene complexes generated catalytically from propargyl esters using Rh (I) catalyst based on electrophilic activation of the alkyne moiety was reported: Shibata, Y.; Noguchi, K.; Tanaka. K. J. Am. Chem. Soc. 2010, 132, 7896-7898.
23. For [3+2] cycloaddition reaction with electron-rich olefins of α, β-unsaturated carbenoids generated catalytically from corresponding diazo compounds with Rh (I) catalyst, see: Lian, Y.; Davies, H. M. L. J. Am. Chem. Soc. 2010, 132, 440-441 and references cited therein.
24. See also: Lu, S.; Jin, T.; Bao, M.; Yamamoto, Y. Org. Lett. 2010, 12, 864-866.
25. For examples of stoichiometiric [3+2] cycloaddition reactions of alkenyl Fischer carbene complexes with two-carbon unit, see the following reviews: (a) Dötz, K. H.; Stendel, J., Jr. Chem. Rev. 2009, 109, 3227-3274.
26. (b) De Meijere, A.; Schirmer, H.; Duetsch, M. Angew. Chem., Int. Ed. 2000, 39, 3964-4002.
27. For examples of similar platinum (II) monophosphine complexcatalyzed cyclization reactions, see: (a) Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070-1071.
28. (b) Kusama, H.; Ebisawa, M.; Funami, H.; Iwasawa, N. J. Am. Chem. Soc. 2009, 131, 16352-16353.
29. 3 improved the yield of the product.
30. For a review on tandem reactions for indole synthesis, see: Barluenga, J.; Rodríguez, F.; Fañanás, F. J. Chem. Asian J. 2009, 4, 1036-1048.
31. The relative configuration of 2g, 2i, and 4d could not be determined by NOE measurement.
32. 3P, 4a was obtained in 73% yield.