Organocatalytic desymmetrization of cyclic meso-anhydrides through enantioselective alcoholysis with functionalized primary nitroallylic alcohols

Tetrahedron

Volumn 70, Issue 47, 2014, Pages 9064-9069

  Chen, Yan Ming ^a   Amireddy, Mamatha ^a   Chen, Kwunmin ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

Desymmetrization; Michael addition; Organocatalysis; Thiourea

Indexed keywords

ACID ANHYDRIDE; ALCOHOL DERIVATIVE; CINCHONIDINE; ESTER; THIOUREA DERIVATIVE;

ALCOHOLYSIS; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DESYMMETRIZATION; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE; HYDROGEN BOND; ORGANOCATALYSIS; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY;

EID: 84922623239     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.10.008     Document Type: Article

References (66)

1. M. Beller, and C. Bolm Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals 2nd ed. 2004 Wiley-VCH Weinheim, Germany
2. I. Ojima Catalytic Asymmetric Synthesis 2nd ed. 2000 Wiley-VCH New York, NY
3. R. Mahrwald Enantioselective Organocatalyzed Reactions 2011 Springer Berlin, Germany
4. H. Pellissier Recent Developments in Asymmetric Organocatalysis Vols. I and II 2010 RSC Cambridge, UK
5. P.I. Dalko Enantioselective Organocatalysis: Reactions and Experimental Procedures 2007 Wiley-VCH Weinheim, Germany For recent reviews on organocatalytic processes, see
6. A. Moyano, and R. Rios Chem. Rev. 111 2011 4703
7. C. Graaff, E. Ruijter, and R.V.A. Orru Chem. Soc. Rev. 41 2012 3969
8. H. Pellissier Adv. Synth. Catal. 354 2012 237
9. K.L. Jensen, G. Dickmeiss, H. Jiang, Ł. Albrecht, and K.A. Jørgensen Acc. Chem. Res. 45 2012 248
10. For review articles, see
11. M.D. Diaz-de-Villegas, J.A. Galvez, R. Badorrey, and M.P. Lopez-Ram-de-Viu Chem. - Eur. J. 18 2012 13920
12. A. Enriquez-Garcia, and E.P. Kundig Chem. Soc. Rev. 41 2012 7803
13. Z. Rodriguez-Docampo, and S.J. Connon ChemCatChem 4 2012 151
14. M.D. Diaz-de-Villegas, J.A. Galvez, P. Etayo, R. Badorrey, and M.P. Lopez-Ram-de-Viu Chem. Soc. Rev. 40 2011 5564
15. I. Atodiresei, I. Schiffers, and C. Bolm Chem. Rev. 107 2007 5683
16. Y. Chen, P. McDaid, and L. Deng Chem. Rev. 103 2003 2965
17. A.C. Spivey, and B.I. Andrews Angew. Chem., Int. Ed. 40 2001 3131
18. J. Nicolas, S. Mura, D. Brambilla, N. Mackiewicz, and P. Couvreur Chem. Soc. Rev. 42 2013 1147
19. A.C. Fogarty, E. Duboué-Dijon, F. Sterpone, J.T. Hynes, and D. Laage Chem. Soc. Rev. 42 2013 5672
20. A.C. Evans, D.A. Longbottom, M. Matsuoka, J.E. Davies, R. Turner, V. Franckevičius, and S.V. Ley Org. Biomol. Chem. 7 2009 747
21. M. Anstiss, and A. Nelson Org. Biomol. Chem. 4 2006 4135
22. Z. Ke, C.K. Tan, F. Chen, and Y.-Y. Yeung J. Am. Chem. Soc. 136 2014 5627
23. Z. Wang, Z. Chen, and J. Sun Angew. Chem., Int. Ed. 52 2013 6685
24. Z. Wang, W.K. Law, and J. Sun Org. Lett. 15 2013 5964
25. M.-Q. Jia, C. Liu, and S.-L. You J. Org. Chem. 77 2012 10996
26. L. Zhou, X. Liu, J. Ji, Y. Zhang, X. Hu, L. Lin, and X. Feng J. Am. Chem. Soc. 134 2012 17023
27. G. Dickmeiss, V. De Sio, J. Udmark, T.B. Poulsen, V. Marcos, and K.A. Jørgensen Angew. Chem., Int. Ed. 48 2009 6650
28. X. Companyó, G. Valero, L. Crovetto, A. Moyano, and R. Rios Chem. - Eur. J. 15 2009 6564
29. K. Ikeuchi, S. Ido, S. Yoshimura, T. Asakawa, M. Inai, Y. Hamashima, and T. Kan Org. Lett. 14 2012 6016
30. G.D. Sala, and A. Lattanzi Org. Lett. 11 2009 3330
31. K. Mori, T. Katoh, T. Suzuki, T. Noji, M. Yamanaka, and T. Akiyama Angew. Chem., Int. Ed. 48 2009 9652
32. D.B. Ramachary, and C.F. Barbas III Org. Lett. 7 2005 1577
33. C.A. Lewis, J.L. Gustafson, A. Chiu, J. Balsells, D. Pollard, J. Murry, R.A. Reamer, K.B. Hansen, and S.J. Miller J. Am. Chem. Soc. 130 2008 16358
34. C. Roux, M. Candy, J.-M. Pons, O. Chuzel, and C. Bressy Angew. Chem., Int. Ed. 53 2014 766
35. M. Yoshida, N. Sassa, T. Kato, S. Fujinami, T. Soeta, K. Inomata, and Y. Ukaji Chem. - Eur. J. 20 2014 2058
36. N.R. Babij, and J.P. Wolfe Angew. Chem., Int. Ed. 52 2013 9247
37. K. Liu, H.-L. Teng, L. Yao, H.-Y. Tao, and C.-J. Wang Org. Lett. 15 2013 2250
38. M. Hayashi, N. Shiomi, Y. Funahashi, and S. Nakamura J. Am. Chem. Soc. 134 2012 19366
39. J.Y. Lee, Y.S. You, and S.H. Kang J. Am. Chem. Soc. 133 2011 1772
40. P. Gopinath, T. Watanabe, and M. Shibasaki Org. Lett. 14 2012 1358
41. U. Piarulli, P. Daubos, C. Claverie, M. Roux, and C. Gennari Angew. Chem., Int. Ed. 42 2003 234
42. R. Shintani, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 1057
43. D. Seebach, G. Jaeschke, and Y.M. Wang Angew. Chem., Int. Ed. Engl. 34 1995 2395
44. H. Fernández-Pérez, P. Etayo, J.R. Lao, J.L. Núñez-Rico, and A. Vidal-Ferran Chem. Commun. 2013 10666
45. J. Hiratake, Y. Yamamoto, and J. Oda J. Chem. Soc., Chem. Commun. 1985 1717
46. J. Hiratake, M. Inagaki, Y. Yamamoto, and J. Oda J. Chem. Soc., Perkin Trans. 1 1987 1053
47. E. Schmitt, I. Schiffers, and C. Bolm Tetrahedron 2010 6349
48. R. Manzano, J.M. Andrés, M.-D. Muruzábal, and R. Pedrosa J. Org. Chem. 75 2010 5417
49. H. Li, X. Liu, F. Wu, L. Tang, and L. Deng Proc. Natl. Acad. Sci. U.S.A. 107 2010 20625
50. A. Peschiulli, Y. Gun'ko, and S.J. Connon J. Org. Chem. 73 2008 2454
51. S.H. Oh, H.S. Rho, J.W. Lee, J.E. Lee, S.H. Youk, J. Chin, and C.E. Song Angew. Chem., Int. Ed. 47 2008 7872
52. A. Peschiulli, C. Quigley, S. Tallon, Y.K. Gun'ko, and S.J. Connon J. Org. Chem. 73 2008 6409
53. C. Bolm, I. Schiffers, C.L. Dinter, and A. Gerlach J. Org. Chem. 65 2000 6984
54. Y. Chen, S.-K. Tian, and L. Deng J. Am. Chem. Soc. 122 2000 9542
55. C.E. Song Cinchona Alkaloids in Synthesis & Catalysis: Ligands, Immobilization and Organocatalysis 2009 Wiley-VCH Weinheim, Germany
56. For review articles, see
57. E.M.O. Yeboah, S.O. Yeboah, and G.S. Singh Tetrahedron 67 2011 1725
58. S.J. Connon Chem. Commun. 2008 2499
59. S.-K. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, and L. Deng Acc. Chem. Res. 37 2004 621 For recent selected examples, see
60. R.P. Singh, K. Bartelson, Y. Wang, H. Su, X. Lu, and L. Deng J. Am. Chem. Soc. 130 2008 2422
61. S.H. McCooey, and S.J. Connon Angew. Chem., Int. Ed. 44 2005 6367
62. 1H NMR dilution experiments.
63. The organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols with simultaneous desymmetrization of prochiral cyclic anhydrides was investigated in our laboratory.
64. The supplementary crystallographic data of 3b (CCDC-979353) can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
65. R.A. Aitken, J. Gopal, and J.A. Hirst J. Chem. Soc., Chem. Commun. 1988 632
66. B. Dedeoglu, S. Catak, K.N. Houk, and V. Aviyente ChemCatChem 2 2010 1122