Organocatalytic asymmetric conjugate additions of oxindoles and benzofuranones to cyclic enones

Synlett

Volumn , Issue 11, 2010, Pages 1704-1708

  Pesciaioli, Fabio ^a   Tian, Xu ^b   Bencivenni, Giorgio ^a   Bartoli, Giuseppe ^a   Melchiorre, Paolo ^b,c  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^c INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

asymmetric catalysis; ketones; Michael addition; organocatalysis; quaternary carbon

Indexed keywords

3 BENZOFURANONE DERIVATIVE; ALKALOID DERIVATIVE; AMINE; OXINDOLE;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CINCHONA; ENANTIOSELECTIVITY; MICHAEL ADDITION; STEREOCHEMISTRY;

EID: 77953878420     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219955     Document Type: Article

References (53)

1. Nicolaou K C., Snyder S A., Proc. Natl. Acad. Sci. U.S.A. 2004 101 11929
2. Shenvi R A., OMalley [nl]D P., Baran P S., Acc. Chem. Res. 2009 42 530
3. Mohr J T., Krout M R., Stoltz B M., Nature (London) 2008 455 323
4. Grondal C, Jeanty M, Enders D, Nature Chem. 2010 2 167
5. Woodward R B., Bader [nl]F E., Bickel H, Frey A J., Kierstead R W., J. Am. Chem. Soc. 1956 78 2023
6. Corey E J., Angew. Chem. Int. Ed. 2002 41 1650
7. Dounay A B., Overman L E., Chem. Rev. 2003 103 2945
8. Newman D J., Cragg G M., J. Nat. Prod. 2007 70 461
9. Stereochemical Aspects of Drug Action and Disposition Eichelbaum M Testa B Somogyi A Springer Berlin 2003
10. Kumar K, Waldmann H, Angew. Chem. Int. Ed. 2009 48 3224
11. Quaternary Stereocenters. Challenges and Solutions in Organic Synthesis Christoffers J Baro A Wiley-VCH Weinheim 2006
12. Douglas C J., Overman L E., Proc. Natl. Acad. Sci. U.S.A. 2004 101 5363
13. Trost B M., Chunhui J, Synthesis 2006 369
14. Bella M, Gasperi T, Synthesis 2009 1583
15. Lin H, Danishefsky S J., Angew. Chem. Int. Ed. 2003 42 36
16. Marti C, Carreira E M., Eur. J. Org. Chem. 2003 2209
17. Galliford C V., Scheidt K A., Angew. Chem. Int. Ed. 2007 46 8748
18. Venkatesan H, Davis M C., Altas Y, Snyder D, Liotta C, J. Org. Chem. 2001 66 3653
19. Lo M M.-C, Neumann C S., Nagayama S, Perlstein E O., Schreiber S L., J. Am. Chem. Soc. 2004 126 16077
20. Kotha S, Deb A C., Lahiri K, Manivannan E, Synthesis 2009 165; and references cited therein, Lik K.-C, So S.-S, Zhang J, Zhang Z, WO 2006/136606 2006, Liu J.-J, Zhang Z, WO 2008/055812 2008
21. Selected examples:, Madin A, ODonnell C J., Oh T, Old D W., Overman L E., Sharp M J., J. Am. Chem. Soc. 2005 127 18054
22. Trost B M., Zhang Y, J. Am. Chem. Soc. 2007 129 14548
23. Kndig E P., Seidel T M., Jia Y, Bernardinelli G, Angew. Chem. Int. Ed. 2007 46 8484
24. Ma S, Han X, Krishnan S, Virgil S C., Stoltz B M., Angew. Chem. Int. Ed. 2009 48 8037
25. Selected examples:, Lee T B. K., Wong G S. K., J. Org. Chem. 1991 56 872
26. Hills I D., Fu G, Angew. Chem. Int. Ed. 2003 42 3921
27. Ogawa S, Shibata N, Inagaki J, Nakamura S, Toru T, Shiro M, Angew. Chem. Int. Ed. 2007 46 8666
28. Tian X, Jiang K, Peng J, Du W, Chen Y.-C, Org.Lett. 2008 10 3583
29. Chen X.-H, Wei Q, Luo S.-W, Xiao H, Gong L.-Z, J. Am. Chem. Soc. 2009 131 13819
30. Bencivenni G, Wu L.-Y, Mazzanti A, Giannichi B, Pesciaioli F, Song M.-P, Bartoli G, Melchiorre P, Angew. Chem. Int. Ed. 2009 48 7200
31. For selected examples on the catalytic construction of adjacent quaternary and tertiary chiral centers, see:, Austin J F., Kim S.-G, Sinz C J., Xiao W.-J, MacMillan D W. C., Proc. Natl. Acad. Sci. U.S.A. 2004 101 5482
32. Li H, Wang Y, Tang L, Wu F, Liu X, Guo C, Foxman B M., Deng L, Angew. Chem. Int. Ed. 2005 44 105
33. Lalonde M P., Chen Y, Jacobsen E N., Angew. Chem. Int. Ed. 2006 45 6366
34. Bartoli G, Bosco M, Carlone A, Cavalli A, Locatelli M, Mazzanti A, Ricci P, Sambri L, Melchiorre P, Angew. Chem. Int. Ed. 2006 45 4966
35. Streuff J, White D E., Virgil S C., Stoltz B M., Nature Chem. 2010 2 192
36. Galzerano P, Bencivenni G, Pesciaioli F, Mazzanti A, Giannichi B, Sambri L, Bartoli G, Melchiorre P, Chem. Eur. J. 2009 15 7846
37. Bui T, Syed S, Barbas C F. III., J. Am. Chem. Soc. 2009 131 8758
38. Kato Y, Furutachi M, Chen Z, Mitsunuma H, Matsunaga S, Shibasaki M, J. Am. Chem. Soc. 2009 131 9168
39. He R, Shirakawa S, Maruoka K, J. Am. Chem. Soc. 2009 131 16620
40. For recent examples on the catalytic, asymmetric addition of oxindoles to vinyl sulfones and vinyl ketones, generating a single, quaternary stereocenter:, He R, Ding C, Maruoka K, Angew. Chem. Int. Ed. 2009 48 4559
41. Li X, Xi Z.-G, Luo S, Cheng J.-P, Org. Biomol. Chem. 2010 8 77
42. Bartoli G, Melchiorre P, Synlett 2008 1759
43. Chen Y.-C, Synlett 2008 1919
44. Martin N J. A., List B, J. Am. Chem. Soc. 2006 128 13368
45. Wang X, Reisinger C M., List B, J. Am. Chem. Soc. 2008 130 6070
46. Selected examples:, Xie J.-W, Chen W, Li R, Zeng M, Du W, Yue L, Chen Y.-C, Wu Y, Zhu J, Deng [nl]J.-G, Angew. Chem. Int. Ed. 2007 46 389
47. Bartoli G, Bosco M, Carlone A, Pesciaioli F, Sambri L, Melchiorre P, Org. Lett. 2007 9 1403
48. Chen W, Du W, Duan Y, Wu Y, Yang S.-Y, Chen Y.-C, Angew. Chem. Int. Ed. 2007 46 7667
49. Zhang E, Fan C.-A, Tu Y.-Q, Zhang F.-M, Song Y.-L, J. Am. Chem. Soc. 2009 131 14626
50. Wu L.-Y, Bencivenni G, Mancinelli M, Mazzanti A, Bartoli G, Melchiorre P, Angew. Chem. Int. Ed. 2009 48 7196
51. Galzerano P, Pesciaioli F, Mazzanti A, Bartoli G, Melchiorre P, Angew. Chem. Int. Ed. 2009 48 7892
52. Bordwell F G., Fried H E., J. Org. Chem. 1991 56 4218
53. For an example of catalytic and enantioselective O-to-C rearrangements of O-acylated benzofuranone derivatives, see ref. 8b. For an early example, see:, Black T H., Arrivo S M., Schumm J S., Knobeloch J M., J. Chem. Soc., Chem. Commun. 1986 1524