Pd-catalyzed diastereoselective allylation of aldehydes with 3-bromomethyl-5H-furan-2-one: Stereoselective synthesis of β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones with a syn configuration

Chemical Communications

Volumn 49, Issue 41, 2013, Pages 4697-4699

  Zhang, Fuhai ^a   Yang, Yanxin ^a   Xie, Longguan ^a   Xu, Xiaohua ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMOMETHYL 5H FURAN 2 ONE; ALDEHYDE DERIVATIVE; BETA(HYDROXYMETHYLARYL ALKYL)ALPHA METHYLENE GAMMA BUTYROLACTONE; CARBON; FURAN DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; STEREOCHEMISTRY;

EID: 84876902164     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc41501e     Document Type: Article

References (33)

1. A. Vasas, J. Hohmann: Nat. Prod. Rep. 2011 28 824
2. H. M. R. Hoffmann, J. Rabe: Angew. Chem., Int. Ed. Engl. 1985 24 94
3. A. K. Picman: Biochem. Syst. Ecol. 1986 14 255
4. O. R. PagÁn, A. L. Rowlands, M. Azam, K. R. Urban, A. H. Bidja, D. M. Roy, R. B. Feeney, L. K. Afshari: Pharmacol., Biochem. Behav. 2008 89 160-170
5. B. Zingarelli, P. W. Hake, A. Denenberg, H. R. Wong: Shock 2002 17 127-134
6. C. Q. Wu, F. Chen, J. W. Rushing, X. Wang, H. J. Kim, G. Huang, V. Haley-Zitlin, G. Q. He: J. Med. Food 2006 9 55-61
7. S. Djeddi, A. Karioti, M. Sokovic, C. Koukoulitsa, H. Skaltsa: Bioorg. Med. Chem. 2008 16 3725-3731
8. S. P. Hehner, T. G. Hofmann, W. Droge, M. L. Schmitz: J. Immunol. 1999 163 5617-5623
9. R. R. A. Kitson, A. Millemaggi, R. J. K. Taylor: Angew. Chem., Int. Ed. 2009 48 9426-9451
10. S. H. Lin, C. C. Chen, W. J. Vong, R. S. Liu: Organometallics 1995 14 1619-1625
11. C. C. Chen, J. S. Fan, S. J. Shieh, G. H. Lee, S. L. Wang, R. S. Liu: J. Am. Chem. Soc. 1996 118 9279-9287
12. L. H. Shiu, S. L. Wang, M. J. Wu, R. S. Liu: J. Chem. Soc., Chem. Commun. 1997 2055-2062
13. M. Chandrasekharam, R. S. Liu: J. Org. Chem. 1998 63 9122-9124
14. H. S. Yang, X. X. Qiao, Q. Cui, X. H. Xu: Chin. Chem. Lett. 2009 20 1023-1024
15. H. S. Yang, Y. Z. Gao, X. X. Qiao, L. G. Xie, X. H. Xu: Org. Lett. 2011 13 3670-3673
16. D. M. Hodgson, E. P. A. Talbot, B. P. Clark: Org. Lett. 2011 13 2594-2597
17. Y. Gao, X. Wang, L. Sun, L. Xie, X. Xu: Org. Biomol. Chem. 2012 10 3991
18. B. M. Trost and I. Fleming, Comprehensive organic synthesis: selectivity, strategy, and efficiency in modern organic chemistry, Pergamon Press, Oxford, England, New York, 1st edn, 1991
19. J. P. Takahara, Y. Masuyama, Y. Kurusu: J. Am. Chem. Soc. 1992 114 2577-2586
20. S. Matsubara, K. Wakamatsu, Y. Morizawa, N. Tsuboniwa, K. Oshima, H. Nozaki: Bull. Chem. Soc. Jpn. 1985 58 1196-1199
21. B. M. Trost, J. W. Herndon: J. Am. Chem. Soc. 1984 106 6835-6837
22. B. M. Trost, J. Yoshida, M. Lautens: J. Am. Chem. Soc. 1983 105 4494-4496
23. S. Torii, H. Tanaka, T. Katoh, K. Morisaki: Tetrahedron Lett. 1984 25 3207-3208
24. Y. Masuyama, Y. Nimura, Y. Kurusu: Tetrahedron Lett. 1991 32 225-228
25. Y. Masuyama, J. P. Takahara, Y. Kurusu: J. Am. Chem. Soc. 1988 110 4473-4474
26. T. Tabuchi, J. Inanaga, M. Yamaguchi: Tetrahedron Lett. 1987 28 215-216
27. S. -F. Zhu, X. -C. Qiao, Y. -Z. Zhang, L. -X. Wang, Q. -L. Zhou: Chem. Sci. 2011 2 1135
28. G. Zanoni, S. Gladiali, A. Marchetti, P. Piccinini, I. Tredici, G. Vidari: Angew. Chem., Int. Ed. 2004 43 846-849
29. K. Yasui, Y. Goto, T. Yajima, Y. Taniseki, K. Fugami, A. Tanaka, Y. Tamaru: Tetrahedron Lett. 1993 34 7619-7622
30. Y. Tamaru, S. Goto, A. Tanaka, M. Shimizu, M. Kimura: Angew. Chem., Int. Ed. Engl. 1996 35 878-880
31. M. Kimura, M. Shimizu, S. Tanaka, Y. Tamaru: Tetrahedron 2005 61 3709-3718
32. M. Kimura, M. Shimizu, K. Shibata, M. Tazoe, Y. Tamaru: Angew. Chem., Int. Ed. 2003 42 3392-3395
33. M. Kimura, T. Tomizawa, Y. Horino, S. Tanaka, Y. Tamaru: Tetrahedron Lett. 2000 41 3627-3629