On water iminium/enamine catalysis: Organocatalytic enantioselective cyclopropanation of α,β-unsaturated aldehydes

Synthesis

Volumn , Issue 4, 2010, Pages 701-713

  Uria, Uxue ^a   Vicario, Jose L ^a   Badía, Dolores ^a   Carrillo, Luisa ^a   Reyes, Efraim ^a   Pesquera, Amaia ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Asymmetric catalysis; Domino reaction; Michael addition; On water reaction; Organocatalysis

Indexed keywords

ASYMMETRIC CATALYSIS; DOMINO REACTIONS; MICHAEL ADDITIONS; ORGANOCATALYSIS; WATER REACTION;

ALDEHYDES; CATALYSIS; CATALYSTS; FUNCTIONAL ELECTRIC STIMULATION; RATE CONSTANTS; REACTION KINETICS;

ADDITION REACTIONS;

ALDEHYDE DERIVATIVE; ENAMINE; MALONIC ACID DERIVATIVE; WATER;

CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLOPROPANATION; ENANTIOSELECTIVITY; MICHAEL ADDITION; REVIEW;

EID: 76349111073     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218645     Document Type: Review

References (67)

1. For some selected general reviews on asymmetric organocatalysis, see:, Melchiorre P, Marigo M, Carlone A, Bartoli G, Angew. Chem. Int. Ed. 2008 47 6138
2. Dondoni A, Massi A, Angew. Chem. Int. Ed. 2008 47 4638
3. Special issue on organocatalysis: Chem. Rev. 2007 107 5413-5883
4. List B, Yang J.-W, Science 2006 313 1584
5. MacMillan D W. C., Nature 2008 455 304
6. List B, Lerner R A., Barbas C F. III, J. Am. Chem. Soc. 2000 122 2395
7. Ahrendt K A., Borths C J., MacMillan D W. C., J. Am. Chem. Soc. 2000 122 4243
8. For some reviews see:, Vicario J L., Badia D, Carrillo L, Synthesis 2007 2065
9. Almaçi D, Alonso D A., Nájera C, Tetrahedron: Asymmetry 2007 18 299
10. Tsogoeva S B., Eur. J. Org. Chem. 2007 1701
11. Sulzer-Mosse S, Alexakis A, Chem. Commun. 2007 3123
12. Yu X, Wang W, Org. Biomol. Chem. 2008 6 2037
13. Enders D, Grondal C, Huettl M R. M., Angew. Chem. Int. Ed. 2007 46 1570
14. Guillena G, Ramon D J., Yus M, Tetrahedron: Asymmetry 2007 18 693
15. Reyes E, Vicario J L., Badia D, Carrillo L, Org. Lett. 2006 8 6135
16. Ruiz N, Reyes E, Vicario J L., Badia D, Carrillo L, Uria U, Chem. Eur. J. 2008 14 9357
17. Uria U, Vicario J L., Badia D, Carrillo L, Chem. Commun. 2007 2509
18. Reyes E, Talavera G, Vicario J L., Badia D, Carrillo L, Angew. Chem. Int. Ed. 2009 48 5701
19. For some reviews, see:, Gruttadauria M, Giacalone F, Noto R, Adv. Synth. Catal. 2009 351 33
20. Brogan A P., Dickerson T J., Janda K D., Angew. Chem. Int. Ed. 2006 45 8100
21. See also, Blackmond D G., Armstrong A, Coombe V, Wells A, Angew. Chem. Int. Ed. 2007 46 3798
22. Jung Y, Marcus R A., J. Am. Chem. Soc. 2007 129 5492
23. Narayan S, Muldoon J, Finn M G., Fokin V V., Kolb H C., Sharpless K B., Angew. Chem. Int. Ed. 2005 44 3275
24. For a recent general review, see:, Chanda A, Fokin V V., Chem. Rev. 2009 109 725
25. Wong H N. C., Hon M.-Y, Tse C.-W, Yip Y.-C, Tanko J, Hudlicky T, Chem Rev. 1989 89 165 See also refs. 14 and 15 and references therein.
26. Special issue on cyclopropanes and related rings: Chem. Rev. 2003 103 931-1648 See also ref. 15 and references therein.
27. Sitachitta N, Gerwick W, J. Nat. Prod. 1998 61 681
28. Martoin E, Quinke K, Spahn H, Mutschler E, Chirality 1989 1 223
29. For a review:, Barlow S M., Sullivan F M., Lines J, Food Chem. Toxicol. 2001 39 407
30. Davoren J E., Martin S F., J. Am. Chem. Soc. 2007 129 510
31. Pietruszka J, Rieche A C. M., Adv. Synth. Catal. 2008 350 1407
32. White J D., Lincoln C M., Yang J, Martin W H. C., Chan D B., J. Org. Chem. 2008 73 4139
33. For a recent review on asymmetric cyclopropanations, see:, Pellissier H, Tetrahedron 2008 64 7041
34. For some examples of organocatalytic asymmetric syntheses of cyclopropanes see:, Kunz R K., MacMillan D W. C., J. Am. Chem. Soc. 2005 127 3240
35. Hartikka A.,Lósarczyk A.T.,Arvidsson P. I., Tetrahedron: Asymmetry 2007 18 1403
36. Hartikka A, Arvidsson P I., J. Org. Chem. 2007 72 5874
37. Zhao Y.-H, Zhao G, Cao W G., Tetrahedron: Asymmetry 2007 18 2462
38. Zhao Y.-H, Zheng C.-W, Zhao G, Cao W.-G, Tetrahedron: Asymmetry 2008 19 701
39. Papageorgiou C D., CubillodeDios M A., Ley S V., Gaunt M J., Angew. Chem. Int. Ed. 2004 43 4641
40. Johansson C C. C., Bremeyer N, Ley S V., Owen D R., Smith S C., Gaunt M J., Angew. Chem. Int. Ed. 2006 45 6024
41. Deng X.-M, Cai P, Ye S, Sun X.-L, Liao W.-W, Li K, Tang Y, Wu Y.-D, Dai L.-X, J. Am. Chem. Soc. 2006 128 9730
42. Liao W.-W, Li K, Tang Y, J. Am. Chem. Soc. 2003 125 13030
43. Kojima S, Suzuki M, Watanabe A, Ohkata K, Tetrahedron Lett. 2006 47 9061
44. Xuan Y.-N, Nie S.-Z, Dong L.-T, Zhang J.-M, Yan M, Org. Lett. 2009 11 1583
45. McCooey S H., McCabe T, Connon S J., J. Org. Chem. 2006 71 7494
46. Inokuma T, Sakamoto S, Takemoto Y, Synlett 2009 1627
47. Arai S, Nakayama K, Ishida T, Shioiri T, Tetrahedron Lett. 1999 40 4215
48. Hansen H M., Longbottom D A., Ley S V., Chem. Commun. 2006 4838
49. See also:, Wascholowski V, Hansen H M., Longbottom D A., Ley S V., Synthesis 2008 1269
50. For related examples, see:, Lv J, Zhang J, Lin Z, Wang Y, Chem. Eur. J. 2009 15 972
51. Vesely J, Zhao G.-L, Bartoszewicz A, Córdova A, Tetrahedron Lett. 2008 49 4209 See also refs. 22 and 23.
52. Companyó X, Alba A.-N, Cárdenas F, Moyano A, Rios R, Eur. J. Org. Chem. 2009 3075
53. Ibrahem I, Zhao G.-L, Rios R, Vesely J, Sundén H, Dziedzic P, Córdova A, Chem. Eur. J. 2008 14 7867
54. Rios R, Sundén H, Vesely J, Zhao G.-L, Dziedzic P, Córdova A, Adv. Synth. Catal. 2007 349 1028
55. Xie H, Zu L, Li H, Wang J, Wang W, J. Am. Chem. Soc. 2007 129 10886
56. For a selected example of acceleration of an organocatalytic Michael reaction via enamine catalysis on water using catalyst 4b see:, Zhu S, Yu S, Ma D, Angew. Chem. Int. Ed. 2008 47 545
57. For some reviews on the use of diarylprolinols as catalysts see:, Palomo C, Mielgo A, Angew. Chem. Int. Ed. 2006 45 7876, Mielgo A, Palomo C, Chem. Asian J. 2008 3 922
58. Mielgo A., Palomo C., C. Chem. Asian J. 2008 3 922
59. Franzén J, Marigo M, Fielenbach D, Wabnitz T C., Kjaersgaard A, Jørgensen K A., J. Am. Chem. Soc. 2005 127 18296
60. See also:, Hayashi Y, Gotoh H, Hayasi T, Shoji M, Angew. Chem. Int. Ed. 2005 44 4212
61. See, for example:, Alza E, Cambeiro X C., Jimeno C, Pericàs M A., Org. Lett. 2007 9 3717
62. Palomo C, Landa A, Mielgo A, Oiarbide M, Puente A, Vera S, Angew. Chem. Int. Ed. 2007 46 8431
63. Mase N, Nakai Y, Ohara N, Yoda H, Takabe K, Tanaka F, Barbas C F. III, J. Am. Chem. Soc. 2006 128 734
64. Mase N, Watanabe K, Yoda H, Takabe K, Yanaka F, Barbas C F. III, J. Am. Chem. Soc. 2006 128 4966
65. Yang H, Carter R G., Org. Lett. 2008 10 4649
66. Pickering L, Malhi B S., Coe P L., Walker R T., Tetrahedron 1995 51 2719
67. Itoh T, Ishikawa H, Hayashi Y, Org. Lett. 2009 11 3854