N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition of ketenes and 3-aroylcoumarins: Highly enantioselective synthesis of dihydrocoumarin-fused dihydropyranones

Organic and Biomolecular Chemistry

Volumn 11, Issue 1, 2013, Pages 158-163

  Jian, Teng Yue ^a   Chen, Xiang Yu ^a   Sun, Li Hui ^a   Ye, Song ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CYCLIZATION; ENANTIOSELECTIVITY;

DIASTEREO-SELECTIVITY; DIHYDROPYRANONES; ENANTIOSELECTIVE SYNTHESIS; HIGH ENANTIOSELECTIVITY; HIGH YIELD; N-HETEROCYCLIC;

ORGANIC COMPOUNDS;

EID: 84870525725     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob26804c     Document Type: Article

References (32)

1. D. A. Horton G. T. Bourne M. L. Smythe Chem. Rev. 2003 103 893
2. R. D. H. Murray, J. Mendez and S. A. Brown, The Natural Coumarins: Occurrence, Chemistry, and Biochemistry, Wiley, New York, 1982
3. R. O'Kennedy and R. D. Thornes, Coumarins: Biology, Applications, and Mode of Action, Wiley, Chichester, UK, 1st edn, 1997
4. E. Alden-Danforth M. T. Scerba T. Lectka Org. Lett. 2008 10 4951
5. H. Alper C. Dong J. Org. Chem. 2004 69 5011
6. T. Matsuda M. Shigeno M. Murakami J. Am. Chem. Soc. 2007 129 12086
7. H. Lv L. You S. Ye Adv. Synth. Catal. 2008 350 2715
8. X. Y. Lu X. L. Han Org. Lett. 2010 12 108
9. H. Staudinger Ber. Dtsch. Chem. Ges. 1905 38 1735
10. H. Staudinger Justus Liebigs Ann. Chem. 1907 356 51
11. T. T. Tidwell Angew. Chem., Int. Ed. 2005 44 5778
12. R. K. Orr M. A. Calter Tetrahedron 2003 59 3545
13. D. H. Paull A. Weatherwax T. Lectka Tetrahedron 2009 65 6771
14. A. E. Taggi A. M. Hafez H. Wack B. Young W. J. Drury III T. Lectka J. Am. Chem. Soc. 2000 122 7831
15. J. Cabrera T. Hellmuth R. Peters J. Org. Chem. 2010 75 4326 4329
16. K. A. Morris K. M. Arendt S. H. Oh D. Romo Org. Lett. 2010 12 3764 3767
17. M. Dochnahl G. C. Fu Angew. Chem., Int. Ed. 2009 48 2391 2393
18. D. Enders O. Niemeier A. Henseler Chem. Rev. 2007 107 5606
19. N. Marion S. Díez-González S. P. Nolan Angew. Chem., Int. Ed. 2007 46 2988
20. J. L. Moore T. Rovis Top. Curr. Chem. 2010 291 77
21. Y.-R. Zhang L. He X. Wu P.-L. Shao S. Ye Org. Lett. 2008 10 277
22. X.-L. Huang L. He P.-L. Shao S. Ye Angew. Chem., Int. Ed. 2009 48 192
23. P.-L. Shao X.-Y. Chen S. Ye Angew. Chem., Int. Ed. 2010 49 8412
24. T.-Y. Jian L. He C. Tang S. Ye Angew. Chem., Int. Ed. 2011 50 9104
25. N. Duguet C. D. Campbell A. M. Z. Slawin A. D. Smith Org. Biomol. Chem. 2008 6 1108
26. C. Concellón N. Duguet A. D. Smith Adv. Synth. Catal. 2009 351 3001
27. Y.-R. Zhang H. Lv D. Zhou S. Ye Chem.-Eur. J. 2008 14 8473
28. M. He G. J. Uc J. W. Bode J. Am. Chem. Soc. 2006 128 15088
29. D. Enders J. Han Tetrahedron: Asymmetry 2008 19 1367
30. L. He Y.-R. Zhang X.-L. Huang S. Ye Synthesis 2008 2825
31. C. E. Cannizzaro T. Strassner K. N. Houk J. Am. Chem. Soc. 2001 123 2668
32. C. E. Cannizzaro K. N. Houk J. Am. Chem. Soc. 2004 126 10992