Phosphane-catalyzed [3+2] annulation of allenoates with aldehydes: A simple and efficient synthesis of 2-alkylidenetetrahydrofurans

Chemistry - A European Journal

Volumn 15, Issue 35, 2009, Pages 8698-8702

  Xu, Silong ^a   Zhou, Lili ^a   Ma, Renqin ^a   Song, Haibin ^a   He, Zhengjie ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Aldehydes; Allenes; Cycloaddition organocatalysis; Phosphanes

Indexed keywords

ALKYLIDENETETRAHYDROFURANS; ALLENES; AROMATIC ALDEHYDE; EFFICIENT SYNTHESIS; HETEROCYCLES; HYDROGEN SHIFTS; NMR SPECTROSCOPY; PHOSPHANES; REACTION CONDITIONS; REACTIVITY PATTERN; STRUCTURAL ASSIGNMENTS; SYNTHETIC BUILDING BLOCKS; TETRAHYDROFURANS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

CATALYSIS; CHROMATOGRAPHIC ANALYSIS; COLUMN CHROMATOGRAPHY; GELATION; HYDROGEN; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS; RATE CONSTANTS; REACTION KINETICS; SILICA; SILICA GEL; SYNTHESIS (CHEMICAL);

ALDEHYDES;

ALDEHYDE; ALKADIENE; ALLENE; FURAN DERIVATIVE; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ALDEHYDES; ALKADIENES; CATALYSIS; FURANS; PHOSPHINES;

EID: 69749123343     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901276     Document Type: Article

References (57)

1. a) M. C. Elliott, E. Williams, J. Chem. Soc. Perkin Trans. 1 2001, 2303-2340:
2. b) A. Mitchenson, A. Nadin. J. Chem. Soc. Perkin Trans. 1 2000. 2862-2892;
3. c) M. C. Elliott, J. Chem. Soc. Perkin Trans 1 2000, 1291-1318;
4. d)T.L.B. Boivin, Tetrahedron 1987, 43, 3309-3362:
5. e) F. O. Alali, X. X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999. 62. 504-540.
6. a) B. M. Trost, C.-J. Li. J. Am. Chem. Soc. 1994. 116, 10819-10820, and references therein;
7. b) X. L. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y. Tong. H. N. C. Wong, Tetrahedron 1998. 54, 1955-2020:
8. c) P. M. Lundin. J. Esquivias. G. C. Fu, Angew. Chem. 2009. 121. 160-162;
9. Angew. Chem. Int. Ed. 2009. 48. 154-156;
10. d) H. Tsujita, Y. Ura. K. Wada, T. Kondo, T. Milsudo, Chem. Commun. 2005. 5100-5102:
11. e) S. Y. Seo. X. Yu, T. J. Marks, J. Am. Chem. Soc. 2009. 131, 263-276:
12. f) A. Dzudza, T. J. Marks, Org. Lett. 2009, 11, 1523-1526:
13. g) Z. Zhang, R. A. Widenhoefer, Angew. Chem. 2007, 119. 287-289;
14. Angew. Chem. Int. Ed. 2007, 46. 283-285;
15. h) C.-Y. Zhou, P. W. H. Chan, C.-M. Che, Org. Lett. 2006, 8, 325-328;
16. i) Y. Deng. J. Li, S. Ma, Chem. Eur. J. 2008, 14, 4263-4266;
17. j) Y. Deng. Y. Yu, S. Ma, J. Org. Chem. 2008, 73. 585-589. and references therein.
18. a) C.-K. Jung, J.-C. Wang. M. J. Krische. J. Am. Chem. Soc. 2004, 126. 4118-4119;
19. b) B. D. Kelly, J. M. Allen, R. E. Tundel, T. H. Lambert, Org. Lett. 2009. 11. 1381-1383.
20. 3-calalyzed [3+2] annulation of ethyl γ-methylallenoate with 6-bromopicolinaldehyde was reported, with the Z configuration incorrectly assigned to the product according to the reported NMR spectroscopy data: X. Meng, Y. Huang, H. Zhao. P. Xie, J. Ma, R. Chen. Org. Lett. 2009. 11, 991-994.
21. E. Bellur, H. Feist. P. Langer. Tetrahedron 2007, 63, 10865-10888.
22. For recent reviews, see: a) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34. 535-544:
23. b) J. L. Methot. W. R. Roush. Adv. Synth. Catal. 2004, 346. 1035-1050:
24. c) V. Nair. R. S. Menon, A. R. Sreekanth. N. Abhilash. A. T. Biju, Acc. Chem. Res. 2006, 39. 520-530:
25. d) S. Ma. Chem. Rev. 2005, 105, 2829-2871;
26. e) S. Ma. Aldrichim. Acta 2007. 40. 91-102.
27. For most recent reports, see: a) Y. Du, X. Lu. J. Org. Chem. 2003. 68, 6463-6465;
28. b) X.-F Zhu. C. E. Henry. O. Kwon. Tetrahedron 2005, 61. 6276-6282;
29. c) L. Jean, A. Marinetti, Tetrahedron Lett. 2006, 47. 2141-2145:
30. d) J. E. Wilson. G. C. Fu. Angew. Chem. 2006. 118. 1454-1457:
31. Angew. Chem. Int. Ed. 2006, 45. 1426-1429:
32. e) A. Scherer. J. A. Gladysz, Tetrahedron Lett. 2006, 47, 6335-6337:
33. f)B. J. Cowen, S. J. Miller. J. Am. Chem. Soc. 2007, 129. 10988-10989:
34. g)C. E. Henry, O. Kwon, Org. Lett. 2007, 9. 3069-3072:
35. h) D. J. Wallace, R. L. Sidda, R. A. Reamer, J. Org. Chem. 2007, 72, 1051-1054:
36. i) F.-B. Nicolas. J. Ludovic, R. Pascal. M. Angela. Tetrahedron 2007, 63. 11920-11927;
37. j) X. Tang. B. Zhang. Z. He, R. Gao. Z. He. Adv. Synth. Catal. 2007, 349, 2007-2017:
38. k) B. Zhang, Z. He. S. Xu, G. Wu. Z. He. Tetrahedron 2008, 64, 9471-9479:
39. l) Y.-Q. Fang. E.N. Jacobsen. J. Am. Chem. Soc. 2008, 130, 5660-5661:
40. m) V. Arnaud. A. Armen, F.-B. Nicolas. R. Pascal, M. Angela. J. Am. Chem. Soc. 2008, 130, 14030-14031;
41. n)X.-F. Zhu, J. Lan, O. Kwon. J. Am. Chem. Soc. 2003, 125, 4716-4717:
42. o) R. P. Wurz, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 12234-12235;
43. p) Y. S. Tran. O. Kwon, Org. Lett. 2005, 7, 4289-4291;
44. q) Y. S. Tran, O. Kwon, J. Am. Chem. Soc. 2007, 129, 12632-12633.
45. a) G. S. Creech, O. Kwon. Org. Lett. 2008. 10. 429-432;
46. b) G. S. Creech, X.-F. Zhu, B. Fonovic, T. Dudding, O. Kwon, Tetrahedron 2008, 64, 6935-6942;
47. c) X.-F. Zhu, C. E. Henry. J. Wang, T. Dudding, O. Kwon, Org. Lett. 2005, 7, 1387-1390;
48. d) X.-F. Zhu, A.-P. Schaffner, R. C. Li, O. Kwon, Org. Lett. 2005. 7, 2977-2980.
49. a) T. Dudding, O. Kwon, E. Mercier, Org. Lett. 2006, 8, 3643-3646;
50. b) E. Mercier, B. Fonovic. C. Henry, O. Kwon, T. Dudding, Tetrahedron Lett. 2007, 48, 3617-3620;
51. c) H. Guo, Q. Xu, O. Kwon, J. Am. Chem. Soc. 2009, 131, 6318-6319.
52. A phosphane-mediated olefination of aldehydes with α-methyl allenoate has been reported : Z. He. X. Tang, Z. He, Phosphorus Sulfur Silicon Relat. Elem. 2008, 183, 1518-1525.
53. 3) of the vinylic proton for (E)-3 is about δ=0.5 ppm downfield from that of their counterpart (Z)-3.
54. In the phosphane-catalyzed [3+2] cycloaddition of allenoales with activated olefins, a stepwise mechanism and the involvement of water in the proton transfer have been confirmed experimentally and theoretically: a) Y. Xia. Y. Liang. Y. Chen, M. Wang, L. Jiao. F. Huang, S. Liu, Y. Li, Z.-X. Yu. J. Am. Chem. Soc. 2007, 129, 3470-3471;
55. b) Y. Liang, S. Liu, Y. Xia. Y. Li, Z.-X. Yu. Chem. Eur. J. 2008, 14, 4361-4373.
56. a) B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933-7935;
57. b) U. Kazmaier, Tetrahedron 1998, 54, 1491-1496.