Reversal of enantioselectivity by tuning the conformational flexibility of phase-transfer catalysts

Angewandte Chemie - International Edition

Volumn 49, Issue 15, 2010, Pages 2772-2776

  Hua, Ming Qing ^a   Cui, Han Feng ^a   Wang, Lian ^a   Nie, Jing ^a   Ma, Jun An ^b  

^a TIANJIN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric synthesis; Conformational flexibility; Conjugate addition; Enantioselectivity; Phase transfer catalysis

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHALCONES; CHIRAL CATALYST; CONFORMATIONAL FLEXIBILITY; CONJUGATE ADDITION; NITROALKANES; PHASE TRANSFER CATALYSIS; PHASE-TRANSFER CATALYSTS; QUATERNARY AMMONIUM SALT;

AMMONIUM COMPOUNDS; CATALYSIS; CATALYSTS; ELECTRON TRANSITIONS; PARAFFINS; SALTS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

2 NITROPROPANE; 2-NITROPROPANE; CHALCONE DERIVATIVE; DRUG DERIVATIVE; NITROALKANE; PROPANE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; PHASE TRANSITION; STEREOISOMERISM;

CATALYSIS; CHALCONES; MOLECULAR CONFORMATION; NITROPARAFFINS; PHASE TRANSITION; PROPANE; QUATERNARY AMMONIUM COMPOUNDS; STEREOISOMERISM;

EID: 77950466555     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906814     Document Type: Article

References (74)

1. a) R. Noyori, Chem. Soc. Rev. 1989, 18. 187;
2. b) Comprehensive Asymmetric Catalysis (Eds.: E.N. Jacobsen, A. Pfaltz. H. Yamamoto), Springer, Berlin, 1999;
3. c) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000.
4. T. P. Dang, H. B. Kagan, J. Chem. Soc. Chem. Commun. 1971, 481.
5. A. Thayer, Chem. Eng. News 2005, 83, 40.
6. T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691.
7. S. J. Malcolmson, S. J. Meek, E. S. Sattely, R. R. Schrock, A. H. Hoveyda, Nature 2008, 456, 933.
8. Selected reviews: a) E. V. Dehmlow, S. S. Dehmlow, Phase Transfer Catalysis, 3rd ed.. VCH, Weinheim, 1993;
9. b) A. Nelson, Angew. Chem. 1999, 111. 1685;
10. Angew. Chem. Int. Ed. 1999, 38, 1583;
11. c) M. J. O'Donnell, Acc. Chem. Res. 2004, 37, 506;
12. d) B. Lygo, B. I. Andrews, Acc. Chem. Res. 2004, 37, 518;
13. e)T. Ooi, K. Maruoka, Angew. Chem 2007, 119, 4300;
14. Angew. Chem. Int. Ed. 2007, 46, 4222;
15. f) S.-s. Jew, H.-g. Park. Chem. Commun. 2009, 7090; selected examples:
16. g) M. J. O'Donnell, W D. Bennett, S. Wu, J. Am. Chem. Soc. 1989, 111, 2353:
17. h) B. Lygo. P. G. Wainwright, Tetrahedron Lett. 1997, 38. 8595;
18. i) E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414;
19. j) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519;
20. k)S.-s. Jew, B.-S. Jeong, M.-S. Yoo, H. Huh, H.-g. Park, Chem. Commun. 2001, 1244;
21. H.-g. Park, B.-S. Jeong, M.-S. Yoo. J.-H. Lee, M.-k. Park, Y.-J. Lee, M.-J. Kim, S.-s. Jew. Angew. Chem. 2002. 114, 3162:
22. Angew. Chem. Int. Ed. 2002. 41, 3036;
23. m) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 5139;
24. n) P. V. Ramachandran, S. Madhi, L. Bland-Berry, M. V. R. Reddy, M. J. O'Donnell, J. Am. Chem. Soc. 2005, 127, 13450;
25. o) T. Ooi, K. Fukumoto, K. Maruoka, Angew. Chem. 2006, 118, 3923;
26. Angew. Chem. Int. Ed. 2006, 45, 3839;
27. p) L. Bernardi, J. López-Cantarero, B. Niess, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 5772;
28. q) R. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. 2008, 120, 9608;
29. Angew. Chem. Int. Ed. 2008. 47. 9466;
30. r) P. Eisner, L. Bernardi, G. D. Salla, J. Over-gaard, K. A. Jørgensen, J. Am. Chem. Soc. 2008. 130, 4897;
31. s) R. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. 2008, 120, 9608;
32. Angew. Chem. Int. Ed. 2008. 47, 9466.
33. a) R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, p. 411;
34. b) N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
35. Recent review: a) O. E. Berner. L. Tedeschi, D. Enders. Eur. J. Org. Chem. 2002. 1788;
36. b) R. Ballini, G. Bosica, D. Fiorini. A. Palmieri. M. Petrini, Chem. Rev. 2005, 105. 933;
37. c) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701; catalysis by metal complexes:
38. d) K. Funabashi, Y. Saida, M. Kanai, T. Arai, H. Sasai, M. Shibasaki, Tetrahedron Lett. 1998, 39, 7557;
39. e) M. S. Taylor, D. N. Zalatan, A. M. Lerchner, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 1313: organocatalysis:
40. f) E. J. Corey, F-Y. Zhang, Org. Lett. 2000, 2, 4257;
41. g) T. Ooi, S. Fujioka, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 11790;
42. h) B. Vakulya, S. Varga, A. Csampai, T. Soós. Org. Lett. 2005. 7, 1967:
43. H. Gotoh, H. Ishikawa, Y. Hayashi, Org. Lett. 2007, 9, 5307.
44. a) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975;
45. b) D. Y. Kim, S. C. Huh, Tetrahedron 2001, 57, 8933;
46. c)T. Novák, J. Tatai, P. Bakó, M. Czugler, G. Keglevich, L. Töke, Synlett 2001, 424;
47. d) T. Bakó, P. Bakó, Á. Szöllõsy, M. Czugler, G. Keglevich, L. Töke, Tetrahedron: Asymmetry 2002, 13, 203;
48. e) N. Hailand, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67. 8331:
49. f) S. B. Tsogoeva, S. Jagtap, Synlett 2004, 2624;
50. g) A. Prieto, N. Hailand, K. A. Jørgensen, Org. Lett. 2005, 7, 3897;
51. h) C. E. T. Mitchell, S. E. Brenner, S.V. Ley, Chem. Commun. 2005, 5346;
52. i) S. Hanessian, Z. Shao, J. S. Warrier, Org. Lett. 2006, 8, 4787;
53. j) J. Wang, H. Li, L. Zuo, W. Wang, Adv. Synth. Catal. 2006. 348, 2047;
54. k) B. Vakulya, S. Varga. T. Soós, J. Org. Chem. 2008, 73, 3475.
55. CCDC 734390 (8j) and 734391 (81) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
56. Reviews: a) M. P. Sibi, M. Liu, Curr. Org. Chem. 2001, 5, 719;
57. b) G. Zanoni, F. Castronovo, M. Franzini, G. Vidari, E. Giannini, Chem. Soc. Rev. 2003, 32, 115;
58. c)T. Tanaka, M. Hayashi, Synthesis 2008, 3361;
59. d) M. Bartók, Chem. Rev. 2009, DOI: 10.1021/cr9002352. and references therein; recent examples:
60. e) D.-M. Du, S.-F. Lu, T. Fang, J. Xu, J. Org. Chem. 2005, 70, 3712:
61. f) N. Kato. T. Mita, M. Kanai, B. Themen. M. Kawano. K. Yamaguchi, H. Danjo, Y. Sei, A. Sato. S. Furusho, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 6768;
62. g) W. Zeng, G. Y. Chen, Y. G. Zhou, Y. X. Li, J. Am. Chem. Soc. 2007, 129, 750;
63. h) W. Q. Wu, Q. Peng, D. X. Dong, X. L. Hou, Y. D. Wu, J. Am. Chem. Soc. 2008, 130, 9717;
64. i) M. I. Burguete, M. Collado, J. Escorihuela, S. V. Luis, Angew. Chem. 2007, 119, 9160;
65. Angew. Chem. Int. Ed. 2007, 46, 9002;
66. j) X.-X. Yan, Q. Peng, Q. Li. K. Zhang, J. Yao, X.-L. Hou, Y.-D. Wu, J. Am. Chem. Soc. 2008, 130, 14362;
67. k) K. Nakayama, K. Maruoka, J. Am. Chem. Soc. 2008, 130, 17666.
68. For the addition of nitroethane to chalcone: adduct isolated in 94 % yield, d.r. = 33:67 (synlanti), e.r. = 93:7 (syn), e.r. = 95.5: 4.5 (anti) (by using catalyst 81).
69. Interestingly, under these conditions the aryl ketone function-ality underwent a complete deoxygenative reduction to form a methylene group.
70. For example, catalyst 81 (1 mol %) was used in the reaction of 2-nitropropane with la on a 30 mmol scale, and delivered adduct (5)-2a in 99% yield with e.r. = 99.0: 1.0: it was recovered in pure form in 97% yield. See the Supporting Information for experimental details for the recycling and reuse of the catalyst.
71. Two monocationic analogues derived from piperidine and 4-methylpiperidine were prepared and used for the addition of 2-nitropropane to chalcone: yield <40%, e.r. = <52.5: 47.5 (see the Supporting Information). These preliminary results suggest that both ammonium centers in 8j and 81 could be involved in the dual activation process of the reactants. In addition, the preparation of the corresponding chiral ammonium salts of carbanions (nitronate and/or malonate) is ongoing, and more data are being accumulated. For achiral ammonium salts of carbanions,
72. see: a) M. T. Reetz. S. Hütte, R. Goddard, J. Am. Chem. Soc. 1993, 115, 9339;
73. b) M.T. Reetz, S. Hütte, R. Goddard, Z. Naturforsch. B 1995, 50, 415;
74. c)M.T. Reetz, H. M. Herzog, R. Goddard, Eur. J. Org. Chem. 2009, 1687.