Lewis base-catalyzed reactions of cyclopropenones: Novel synthesis of mono- or multi-substituted allenic esters

Chemical Communications

Volumn 50, Issue 1, 2014, Pages 115-117

  Yang, Yuan Liang ^a   Zhang, Zhen ^a   Zhang, Xiao Nan ^a   Wang, De ^a   Wei, Yin ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALICYCLIC COMPOUND; ALLENIC ESTER; CYCLOPROPENONE DERIVATIVE; ESTER DERIVATIVE; HYDROGEN; LEWIS BASE; NITROGEN; NUCLEOPHILE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; NUCLEOPHILICITY; PROCESS OPTIMIZATION; ROOM TEMPERATURE;

EID: 84888598023     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc46470a     Document Type: Article

References (43)

1. R. Breslow, R. R. Haynie, J. Mirra, J. Am. Chem. Soc., 1959, 81, 247
2. D. N. Kursanov, M. E. Volpin, Y. D. Koreshkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1959, 560
3. H. Tokuyama, M. Isaka, E. Nakamura, Y. Morinaka, J. Antibiot., 1992, 45, 1148
4. R. Ando, Y. Morinaka, J. Am. Chem. Soc., 1993, 115, 1174
5. R. Ando, T. Sakaki, Y. Morinaka, C. Takahashi, Y. Tamao, N. Yoshii, S. Katayama, K.-I. Saito, H. Tokuyama, M. Isaka, E. Nakamura, Bioorg. Med. Chem., 1999, 7, 571
6. K. T. Potts, J. S Baum, Chem. Rev., 1974, 74, 189
7. T. Eicher, J. L. Weber, Top. Curr. Chem., 1975, 57, 1
8. K. Komatsu, T. Kitagawa, Chem. Rev., 2003, 103, 1371
9. A. Hamada, T. Takizawa, Chem. Pharm. Bull., 1975, 23, 2933
10. Y. Wei, M. Shi, Chem. Rev., 2013, 113, 6659
11. Y. Wei, M. Shi, Acc. Chem. Res., 2010, 43, 1005
12. A. Kascheres, D. Marchi, J. Org. Chem., 1975, 40, 2985
13. Y. Tamura, H. Matsushima, M. Ikeda, Tetrahedron, 1975, 32, 431
14. K. N. Hemming, M. V. R. Khan, V. Kondakal, A. Pitard, M. I. R. Qamar, C. Rice, Org. Lett., 2012, 14, 126
15. A. Hamada, T. Takizawa, Chem. Pharm. Bull., 1975, 23, 2933
16. M. Alajarvín, C. López-Leonardo, á. álvarez-García, P. Llamas-Lorente, P. Sánchez-Andrada, J. Berná, A. Pastor, D. G. Baustista, P. Jones, Chem. Eur. J., 2010, 16, 3728
17. S. Patai, The Chemistry of Ketenes, Allenes and Related Compounds, Wiley, New York, 1980
18. S. R. Landor, The Chemistry of the Allenes, Academic Press, London, 1982
19. R. W. Bates, V. Satcharoen, Chem. Soc. Rev., 2002, 31, 12
20. R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev., 2000, 100, 3067
21. Modern Allene Chemistry, ed. N. Krause and A. S. K. Hashmi, Wiley-VCH, Weinheim, Germany, 2004
22. A. Barbero, F. J. Pulido, Synthesis, 2004, 779
23. S. Ma, Chem. Rev., 2005, 105, 2829
24. S. Yu, S. Ma, Angew. Chem., Int. Ed., 2012, 51, 3074
25. D. W. C. MacMillan, J. Am. Chem. Soc., 2002, 124, 13646
26. S. Ma, H. Ren, Q. Wei, J. Am. Chem. Soc., 2003, 125, 4817
27. J. E. Wilson, G. C. Fu, Angew. Chem., Int. Ed., 2006, 45, 1426
28. S. Ma, Z. Gu, J. Am. Chem. Soc., 2006, 128, 4942
29. Y. S. Tran, O. Kwon, J. Am. Chem. Soc., 2007, 129, 12632
30. C. E. Henry, O. Kwon, Org. Lett., 2007, 9, 3069
31. Y. Li, H. Zou, J. Gong, J. Xiang, T. Luo, J. Quan, G. Wang, Z. Yang, Org. Lett., 2007, 9, 4057
32. C. Zhou, C. Fu, S. Ma, Angew. Chem., Int. Ed., 2007, 46, 4379
33. Z. Lu, S. Zheng, X. Zhang, X. Lu, Org. Lett., 2008, 10, 3267
34. B. J. Cowen, L. B. Saun-ders, S. J. Miller, J. Am. Chem. Soc., 2009, 131, 6105
35. X. Guan, Y. Wei, M. Shi, J. Org. Chem., 2009, 74, 6343
36. Q.-M. Zhang, L. Yang, X.-F. Tong, J. Am. Chem. Soc., 2010, 132, 2550
37. G. Chai, S. Wu, C. Fu, S. Ma, J. Am. Chem. Soc., 2011, 133, 3740
38. X.-N. Zhang, H.-P. Deng, L. Huang, Y. Wei, M. Shi, Chem. Commun., 2012, 48, 8664
39. K. M. Brummond, J. E. DeForrest, Synthesis, 2007, 795
40. S. Yu, S. Ma, Chem. Commun., 2011, 47, 5384
41. H. Lu, D. Leow, K.-W. Huang, C.-H. Tan, J. Am. Chem. Soc., 2009, 131, 7212
42. W. Zhang, H. Xu, H. Xu, W. Tang, J. Am. Chem. Soc., 2009, 131, 3832
43. W. Zhang, S. Zheng, N. Liu, J. B. Werness, I. A. Guzei, W. Tang, J. Am. Chem. Soc., 2010, 132, 3664