Organocatalytic enantioselective multicomponent reactions (OEMCRs)

Tetrahedron Asymmetry

Volumn 18, Issue 6, 2007, Pages 693-700

  Guillena, Gabriela ^a   Ramón, Diego J ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; BIGINELLI REACTION; CATALYSIS; CATALYST; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; MANNICH REACTION; MICHAEL ADDITION; ORGANIC CHEMISTRY; PRIORITY JOURNAL; REDUCTION; REVIEW; STEREOCHEMISTRY;

EID: 34247172950     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.03.002     Document Type: Review

References (118)

1. In: Helmchen G., Hoffman R.W., and Mulzer J. (Eds). Stereoselective Synthesis (Houben-Weyl) Vols. 1-10 (1996), Thieme, Stuttgart
2. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vols. 1-3 (1999), Springer, Berlin
3. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis (2004), Springer, Berlin Suppl. 1-2
4. In: Blaser H.U., and Schmidt E. (Eds). Asymmetric Catalysis on Industrial Scale-Challenges, Approaches and Solutions (2004), Wiley-VCH, Weinheim
5. In: Francotte E., and Lindner W. (Eds). Chirality in Drug Research (2006), Wiley-VCH, Weinheim
6. Trost B.M. Science 254 (1991) 1471-1477
7. Sheldon R.A. Pure Appl. Chem. 72 (2000) 1233-1246
8. Trost B.M. Acc. Chem. Res. 35 (2002) 695-705
9. Trost B.M., Frederiksen M.U., Mathias U., and Rudd M.T. Angew. Chem., Int. Ed. 44 (2005) 6630-6666
10. Guillena, G.; Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, doi:10.1002/anie.200603794.
11. For very recent reviews, see:. In: Zhu J., and Bienaymé H. (Eds). Multicomponent Reactions (2005), Wiley-VCH, Weinheim
12. Wessjohann L.A., and Ruijter E. Mol. Diversity 9 (2005) 159-169
13. Ramón D.J., and Yus M. Angew. Chem., Int. Ed. 44 (2005) 1602-1634
14. Nair V., Menon R.S., and Sreekumar V. Pure Appl. Chem. 77 (2005) 1191-1198
15. Dömling A. Chem. Rev. 106 (2006) 17-89
16. Dondoni A., and Massi A. Acc. Chem. Res. 39 (2006) 451-463
17. Mironov M.A. QSAR Comb. Sci. 25 (2006) 423-431
18. Lieby-Muller F., Simon C., Constantieux T., and Rodriguez J. QSAR Comb. Sci. 25 (2006) 432-438
19. Tietze L.F., and Beifuss U. Angew. Chem., Int. Ed. Engl. 32 (1993) 131-163
20. Tietze L.F. Chem. Rev. 96 (1996) 115-136
21. Tietze L.F., and Rackelmann N. Pure Appl. Chem. 76 (2004) 1967-1983
22. de Meijere A., von Zezschwitz P., and Bräse S. Acc. Chem. Res. 38 (2005) 413-422
23. Tejedor D., González-Cruz D., Santos-Exposito A., Marrero-Tellado J.J., de Armas P., and García-Tellado F. Chem. Eur. J. 11 (2005) 3502-3510
24. Pellissier H. Tetrahedron 62 (2006) 1619-1665
25. Pellissier H. Tetrahedron 62 (2006) 2143-2173
26. Ho T.-L. Tandem Organic Reaction (1992), Wiley, New York
27. Pearson P.J., Penkett C.S., and Shell A.J. Chem. Rev. 96 (1996) 115-136
28. Balme G. Angew. Chem., Int. Ed. 43 (2004) 6238-6241
29. Padwa A. Pure Appl. Chem. 76 (2004) 1933-1952
30. Wasilke J.-C., Obrey S.J., Baker R.T., and Bazan G.C. Chem. Rev. 105 (2005) 1001-1020
31. Guo H.-C., and Ma J.-A. Angew. Chem., Int. Ed. 45 (2006) 354-366
32. Lautens M., Alberico D., Bressy C., Fang Y.-Q., Mariampillai B., and Wilhelm T. Pure Appl. Chem. 78 (2006) 351-361
33. Hoffmann H.M.R. Angew. Chem., Int. Ed. Engl. 31 (1992) 1332-1334
34. Wang K.K. Chem. Rev. 96 (1996) 207-222
35. Padwa A., and Weingarten M.D. Chem. Rev. 96 (1996) 223-269
36. Veum L., and Hanefeld U. Chem. Commun. (2006) 825-831
37. Balme G., Bouyssi D., and Monteiro N. Pure Appl. Chem. 78 (2006) 231-239
38. Ihara M. ARKIVOC vii (2006) 416-438
39. Nicolaou K.C., Edmonds D.J., and Bulger P.G. Angew. Chem., Int. Ed. 45 (2006) 7134-7186
40. For a clear differentiation between domino, tandem and cascade transformations, see:. Fogg D.E., and dos Santos E.N. Coord. Chem. Rev. 248 (2004) 2365-2379
41. Chapman C.J., and Frost C.G. Synthesis (2007) 1-21
42. For reviews covering different aspects on this topic, see:. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 40 (2001) 3726-3748
43. List B. Synlett (2001) 1675-1686
44. Jarvo E.R., and Miller S.J. Tetrahedron 58 (2002) 2481-2495
45. Benaglia M., Puglivi A., and Cozzi F. Chem. Rev. 103 (2003) 3401-3430
46. In: Houk K.N., and List B. (Eds). Acc. Chem. Res. 37 (2004) 487-631
47. Pihko P.M. Angew. Chem., Int. Ed. 43 (2004) 2062-2064
48. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
49. Berkessel A., and Gröger H. Asymmetric Organocatalysis-From Biomimetic Concepts to Applications in Asymmetric Synthesis (2005), Wiley-VCH, Weinheim
50. Seayad J., and List B. Org. Biomol. Chem. 3 (2005) 719-724
51. Lelais G., and McMillan D.W.C. Aldrichim. Acta 39 (2006) 79-87
52. Taylor M.S., and Jacobsen E.N. Angew. Chem., Int. Ed. 45 (2006) 1520-1543
53. List B. Chem. Commun. (2006) 819-824
54. Wessig P. Angew. Chem., Int. Ed. 45 (2006) 2168-2171
55. Connon S.J. Angew. Chem., Int. Ed. 45 (2006) 3909-3912
56. Marigo M., and Jørgensen K.A. Chem. Commun. (2006) 2001-2011
57. Connon S.J. Chem. Eur. J. 12 (2006) 5418-5427
58. Guillena G., and Ramón D.J. Tetrahedron: Asymmetry 17 (2006) 1465-1492
59. Palomo C., and Mielgo A. Angew. Chem., Int. Ed. 45 (2006) 7876-7880
60. Gaunt M.J., Johansonn C.C.C., McNally A., and Vo N.T. Drug Discovery Today 12 (2007) 8-27
61. During the preparation of this paper, two reviews have appeared, dealing with the marriage of organocatalysis with either cascade or domino processes:. Rueping M. Nachr. Chem. 55 (2007) 35-37
62. Enders D., Grondal C., and Hüttl M.R.M. Angew. Chem., Int. Ed. 46 (2007) 1570-1581
63. One of the typical mistakes in this field is to assign a multicomponent reaction to an actual one-pot sequential process, in which two reagents are allowed to react for a certain time, after which a third reagent is added. A multicomponent reaction requires the addition of all the reagents at the same time, see for example:. Pan S.C., and List B. Org. Lett. 9 (2007) 1149-1151
64. For reviews see:. Arend M., Westermann B., and Risch N. Angew. Chem., Int. Ed. 37 (1998) 1044-1070
65. Córdova A. Acc. Chem. Res. 37 (2004) 102-112
66. Marques M.M.B. Angew. Chem., Int. Ed. 37 (1998)
67. Angew. Chem., Int. Ed. 45 (2006) 348-352
68. List B. J. Am. Chem. Soc. 122 (2000) 9336-9337
69. Pojarliev P., Biller W.T., Martin H.J., and List B. Synlett (2003) 1903-1905
70. List B., Pojarliev P., Biller W.T., and Martin H.J. J. Am. Chem. Soc. 124 (2002) 827-833
71. Bahmanyar S., and Houk K.N. Org. Lett. 5 (2003) 1249-1251
72. Mauksch M., Tsogoeva S.B., Martynova I.M., and Wei S. Angew. Chem., Int. Ed. 46 (2007) 393-396
73. Notz W., Watanabe S.-i., Chowdari N.S., Zhong G., Betancort J.M., Tanaka F., and Barbas III C.F. Adv. Synth. Catal. 346 (2004) 1131-1140
74. Westermann B., and Neuhaus C. Angew. Chem., Int. Ed. 44 (2005) 4077-4079
75. Enders D., Grondal C., and Vrettou M. Synthesis (2006) 3597-3604
76. Ibrahem I., Zou W., Xu Y., and Córdova A. Adv. Synth. Catal. 348 (2006) 211-222
77. Ibrahem I., Casas J., and Córdova A. Angew. Chem., Int. Ed. 43 (2004) 6528-6531
78. Ibrahem I., Zou W., Casas J., Sundén H., and Córdova A. Tetrahedron 62 (2006) 357-364
79. Chowdari N.S., Ramachary D.B., and Barbas III C.F. Synlett (2003) 1906-1909
80. Hayashi Y., Tsuboi W., Shoji M., and Suzuki N. J. Am. Chem. Soc. 125 (2003) 11208-11209
81. Rodríguez B., and Bolm C. J. Org. Chem. 71 (2006) 2888-2891
82. Hosseini M., Stiasni N., Barbieri V., and Kappe C.O. J. Org. Chem. 72 (2007) 1417-1424
83. Kantam M.L., Rajasekhar C.V., Gopikrishna G., Reddy K.R., and Choudary B.M. Tetrahedron Lett. 48 (2006) 5965-5967
84. Notz W., Sakthivel K., Bui T., Zhong G., and Barbas III C.F. Tetrahedron Lett. 42 (2001) 199-201
85. Enders D., Grondal C., Vrettou M., and Raabe G. Angew. Chem., Int. Ed. 44 (2005) 4079-4083
86. Ibrahem I., Zou W., Engqvist M., Xu Y., and Córdova A. Chem. Eur. J. 11 (2005) 7024-7029
87. Chowdari N.S., Ahmad M., Albertshofer K., Tanaka F., and Barbas III C.F. Org. Lett. 8 (2006) 2839-2842
88. Sasaoka A., Uddin M.I., Shimomoto A., Ichikawa Y., Shiro M., and Kotsuki H. Tetrahedron: Asymmetry 17 (2006) 2963-2969
89. Ramasastry S.S.V., Zhang H., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 129 (2007) 288-289
90. Hayashi Y., Tsuboi W., Ashimine I., Urushima T., Shoji M., and Sakai K. Angew. Chem., Int. Ed. 42 (2003) 3677-3680
91. Córdova A. Synlett (2003) 1651-1654
92. Notz W., Tanaka F., Watanabe S.-i., Chowdari N.S., Turner J.M., Thayumanavan R., and Barbas III C.F. J. Org. Chem. 68 (2003) 9624-9634
93. Córdova A. Chem. Eur. J. 10 (2004) 1987-1997
94. Ibrahem I., and Córdova A. Tetrahedron Lett. 46 (2005) 2839-2843
95. Hayashi Y., Urushima T., Shin M., and Shoji M. Tetrahedron 61 (2005) 11393-11404
96. Liao W.-W., Ibrahem I., and Córdova A. Chem. Commun. (2006) 674-676
97. For a recent review, see:. Tararov V.I., and Börner A. Synlett (2005) 203-211
98. Stoter R.I., Carrera D.E., Ni Y., and MacMillan D.W.C. J. Am. Chem. Soc. 128 (2006) 84-86
99. Hoffmann S., Nicoletti M., and List B. J. Am. Chem. Soc. 128 (2006) 13074-13075
100. For reviews, see:. Kappe C.O. Acc. Chem. Res. 33 (2000) 879-888
101. Kappe C.O. QSAR Comb. Sci. 22 (2003) 630-645
102. Aron Z.D., and Overman L.E. Chem. Commun. (2004) 253-265
103. Chen X.-H., Xu X.-Y., Liu H., Cun L.-F., and Gong L.-Z. J. Am. Chem. Soc. 128 (2006) 14802-14803
104. Ramachary D.B., Chowdari N.S., and Barbas III C.F. Angew. Chem., Int. Ed. 42 (2003) 4233-4237
105. Ramachary D.B., Anebouselvy K., Chowdari N.S., and Barbas III C.F. J. Org. Chem. 69 (2004) 5838-5849
106. Ramachary D.B., and Barbas III C.F. Chem. Eur. J. 10 (2004) 5323-5331
107. Sundén H., Ibrahem I., Eriksson L., and Córdova A. Angew. Chem., Int. Ed. 44 (2005) 4877-4880
108. Liu H., Cun L.-F., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. Org. Lett. 8 (2006) 6023-6026
109. Komnenos T. Justus Liebigs Ann. Chem. 218 (1883) 145-169
110. For reviews, see:. Rossiter B.E., and Swingle N.M. Chem. Rev. 92 (1992) 771-806
111. Krause N., and Gerold A. Angew. Chem., Int. Ed. 36 (1997) 186-204
112. Christoffers J. Chem. Eur. J. 9 (2003) 4862-4867
113. Betancort J.M., Sakthivel K., Thayumanava R., and Barbas III C.F. Tetrahedron Lett. 42 (2001) 4441-4444
114. Huang Y., Walji A.M., Larsen C.H., and MacMillan D.W.C. J. Am. Chem. Soc. 127 (2005) 15051-15053
115. Marigo M., Schulte T., Franzén J., and Jørgensen K.A. J. Am. Chem. Soc. 127 (2005) 15710-15711
116. Enders D., Hüttl M.R.M., Grondal C., and Raabe G. Nature 441 (2006) 861-863
117. Enders D., Hüttl M.R.M., Runsink J., Raabe G., and Wendt B. Angew. Chem., Int. Ed. 46 (2007) 467-469
118. Chowdari N.S., Ramachary D.B., and Barbas III C.F. Org. Lett. 5 (2003) 1685-1688