Pd(0)-catalyzed amphiphilic allylation of aldehydes with vinyl epoxide

Journal of the American Chemical Society

Volumn 129, Issue 14, 2007, Pages 4122-4123

  Kimura, Masanari ^a   Mukai, Ryutaro ^a   Tamaki, Takato ^a   Horino, Yoshikazu ^a,b   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; EPOXIDE; PALLADIUM; VINYL DERIVATIVE;

ALLYLATION; ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 34247113818     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0687320     Document Type: Article

References (24)

1. (a) Tsuji, J. Palladium-Catalyzed Nucleophilic Substitution Involving Allylpalladium, Propargylpalladium, and Related Derivatives in Handbook Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002; Vol. 2, p 1669.
2. (b) Tsuji, J. Transition Metal Reagents and Catalysts; John Wiley & Sons: Chichester, 2000; Chapter 4.
3. Tamaru, Y. Palladium-Catalyzed Reactions of Allyl and Related Derivatives with Organoelectrophiles. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002; Vol. 2, p 1917.
4. Mukai, R.; Horino, Y.; Tanaka, S.; Tamaru, Y.; Kimura, M. J. Am. Chem. Soc. 2004, 126, 11138.
5. Kimura, M.; Horino, Y.; Mukai, R.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2001, 123, 10401.
6. Umpolung of allyl alcohols and vinyl epoxides: (a) Olsson, V. J.; Sebelius, S.; Selander, N.; Szabó, K. J. J. Am. Chem. Soc. 2006, 128, 4588.
7. (b) Shimizu, M.; Kimura, M.; Tamaru, Y. Chem. Eur. J. 2005, 11, 6629.
8. (c) Zhu, S.-F.; Yang, Y.; Liu, B.; Zhou, Q.-L. Org. Lett. 2005, 7, 2333.
9. (d) Kimura, M.; Shimizu, M.; Tanaka, S.; Tamaru, Y. Tetrahedron 2005, 61, 3709.
10. (e) Kimura, M.; Shimizu, M.; Shibata, K.; Tazoe, M.; Tamaru, Y. Angew. Chem. Int. Ed. 2003, 42, 3392.
11. (f) Araki, S.; Kameda, K.; Tanaka, J.; Hirashita, T.; Yamamura, H.; Kawai, M. J. Org. Chem. 2001, 66, 7919.
12. (a) Trost, B. M.; Xie, J. J. Am. Chem. Soc. 2006, 128, 6044.
13. (b) Nishimura, T.; Uemura, S. Synlett 2004, 201.
14. (c) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517.
15. Palladium-catalyzed cyclobutenol synthesis via C2-C3 bond formation: Salem, B.; Suffert, J. Anqew. Chem., Int. Ed. 2004, 43, 2826.
16. (a) Tsuda, T.; Tokai, M.; Ishida, T.; Saegusa, T. J. Org. Chem. 1986, 51, 5216.
17. (b) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969.
18. 8b and ester enolates: (c) Elliott, M. R.; Dhimane, A.-L.; Malacria, M. Tetrahedron Lett. 1998, 39, 8849.
19. 2 for 20 h. (Chemical Equation Presented)
20. Suzuki, S.; Fujita, Y.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1986, 27, 69.
21. α-Allylation of cyclohexanone silyl enol ether with vinyl epoxide without details: Tsuji, J. Pure Appl. Chem. 1986, 56, 869.
22. 3B.
23. 2 may be speculative, it would be feasible due to the ring strain and cis orientation of the substituents. Note the ready retro-ene reaction of 2k to 5 at rt.
24. In DMSO (2.5 mL), under otherwise identical conditions, the first allylation proceeded smoothly (2 h, rt), but the second allylation was very slow and required heating at 50°C for 84 h, yielding trans-2c (31%) as a single isomer.