Highly diastereo- and enantioselective direct aldol reactions promoted by water-compatible organocatalysts bearing a pyrrolidinyl-camphor structural scaffold

Tetrahedron

Volumn 65, Issue 15, 2009, Pages 2879-2888

  Tzeng, Zheng Hao ^a   Chen, Hung Yao ^a   Reddy, Raju Jannapu ^a   Huang, Ching Ting ^a   Chen, Kwunmin ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CAMPHOR DERIVATIVE; CYCLOHEXANE; ORGANIC SOLVENT; PYRROLE DERIVATIVE; WATER;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

DRYOBALANOPS;

EID: 61549115352     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.022     Document Type: Article

References (93)

1. For recent reviews on organocatalysis, see:
2. List B. Tetrahedron 58 (2002) 5573-5590
3. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
4. Pellissier H. Tetrahedron 63 (2007) 9267-9331
5. Dondoni A., and Massi A. Angew. Chem., Int. Ed. 47 (2008) 4638-4660
6. Special issues on organocatalysis, see:
7. Chem. Rev. 107 (2007)
8. Acc. Chem. Res. 37 (2004)
9. Dalko P.I. Enantioselective Organocatalysis (2007), Wiley-VCH, Weinheim
10. Berkessel A., and Groger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis (2005), Wiley-VCH, Weinheim
11. Carreira E.M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Mukaiyama Aldol Reaction. Comprehensive Asymmetric Catalysis Vol. III (1999), Springer, Heidelberg Chapter 29.1
12. For reviews, see:
13. Mahrwald R. Chem. Rev. 99 (1999) 1095-1120
14. Johnson J.S., and Evans D.A. Acc. Chem. Res. 33 (2000) 325-335
15. Machajewski T.D., and Wong C.-H. Angew. Chem., Int. Ed. 39 (2000) 1352-1374
16. Mukaiyama T. Angew. Chem., Int. Ed. 43 (2004) 5590-5614
17. Palomo C., Oiarbide M., and Garcia J.M. Chem. Soc. Rev. 33 (2004) 65-75
18. Kazmaier U. Angew. Chem., Int. Ed. 44 (2005) 2186-2188
19. Guillena G., Nájera C., and Ramón D.J. Tetrahedron: Asymmetry 18 (2007) 2249-2293
20. List B., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 122 (2000) 2395-2396
21. Notz W., and List B. J. Am. Chem. Soc. 122 (2000) 7386-7387
22. List B., Pojarliev P., and Castello C. Org. Lett. 3 (2001) 573-575
23. Bogevig A., Kumaragurubaran N., and Jørgensen K.A. Chem. Commun. (2002) 620-621
24. Northrup A.B., Mangion I.K., Hettche F., and MacMillan D.W.C. Angew. Chem., Int. Ed. 43 (2004) 2152-2154
25. Chan V., Kim J.G., Jimeno C., Carroll P.J., and Walsh P.J. Org. Lett. 6 (2004) 2051-2053
26. Samanta S., Liu J., Dodda R., and Zhao C.-G. Org. Lett. 7 (2005) 5321-5323
27. Kano T., Takai J., Tokuda O., and Maruoka K. Angew. Chem., Int. Ed. 44 (2005) 3055-3057
28. Tang Z., Yang Z.-H., Chen X.-H., Cun L.-F., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. J. Am. Chem. Soc. 127 (2005) 9285-9289
29. Chen J.-R., Lu H.-H., Li X.-Y., Cheng L., Wan J., and Xiao W.-J. Org. Lett. 7 (2005) 4543-4545
30. Gu L., Yu M., Wu X., Zhang Y., and Zhao G. Adv. Synth. Catal. 348 (2006) 2223-2228
31. Luo S., Xu H., Li J., Zhang L., and Cheng J.-P. J. Am. Chem. Soc. 129 (2007) 3074-3075
32. Liu X.-W., Le T.N., Lu Y., Xiao Y., Ma J., and Li X. Org. Biomol. Chem. 6 (2008) 3997-4003
33. For organic reactions in aqueous media, see:
34. Jung Y., and Marcus R.A. J. Am. Chem. Soc. 129 (2007) 5492-5502
35. Brogan A.P., Dickerson T.J., and Janda K.D. Angew. Chem., Int. Ed. 45 (2006) 8100-8102
36. Hayashi Y. Angew. Chem., Int. Ed. 45 (2006) 8103-8104
37. Lindstrom U.M. Chem. Rev. 102 (2002) 2751-2772
38. Li C.-J., and Chan T.H. Organic Reactions in Aqueous Media (1997), John Wiley and Sons, New York, NY
39. Reymond J.-L., and Chen Y. J. Org. Chem. 60 (1995) 6970-6979
40. Cordova A., Notz W., and Barbas III C.F. Chem. Commun. (2002) 3024-3025
41. Peng Y.-Y., Ding Q.-P., Li Z., Wang P.G., and Cheng J.-P. Tetrahedron Lett. 44 (2003) 3871-3875
42. Chimni S.S., Mahajan D., and Babu V.V.S. Tetrahedron Lett. 46 (2005) 5617-5619
43. Hayashi Y., Aratake S., Itoh T., Okano T., Sumiya T., and Shoji M. Chem. Commun. (2007) 957-959
44. Torii H., Nakadai M., Ishihara K., Saito S., and Yamamoto H. Angew. Chem., Int. Ed. 43 (2004) 1983-1986
45. Cordova A., Zou W., Ibrahem I., Reyes E., Engqvist M., and Liao W.-W. Chem. Commun. (2005) 3586-3588
46. Zou W., Ibrahem I., Dziedzic P., Sunden H., and Cordova A. Chem. Commun. (2005) 4946-4948
47. Ward D.E., and Jheengut V. Tetrahedron Lett. 45 (2004) 8347-8350
48. Dziedzic P., Zou W., Ibrahem I., Sunden H., and Cordova A. Tetrahedron Lett. 47 (2006) 6657-6661
49. Gruttadauria M., Giacalone F., Marculescu A.M., and Noto R. Adv. Synth. Catal. 350 (2008) 1397-1405
50. Doherty S., Knight J.G., McRae A., Harrington R.W., and Clegg W. Eur. J. Org. Chem. (2008) 1759-1766
51. For organocatalytical asymmetric aldol reaction in water, see:
52. Mase N., Nakai Y., Ohara N., Yoda H., Takabe K., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 128 (2006) 734-735
53. Jiang Z., Liang Z., Wu X., and Lu Y. Chem. Commun. (2006) 2801-2803
54. Wu Y., Zhang Y., Yu M., Zhao G., and Wang S. Org. Lett. 8 (2006) 4417-4420
55. Huang J., Zhang X., and Armstrong D.W. Angew. Chem., Int. Ed. 46 (2007) 9073-9077
56. Aratake S., Itoh T., Okano T., Usui T., Shoji M., and Hayashi Y. Chem. Commun. (2007) 2524-2526
57. Wu X., Jiang Z., Shen H.-M., and Lu Y. Adv. Synth. Catal. 349 (2007) 812-816
58. Luo S., Xu H., Li J., Zhang L., Mi X., Zheng X., and Cheng J.-P. Tetrahedron 63 (2007) 11307-11314
59. Teo Y.-C. Tetrahedron: Asymmetry 18 (2007) 1155-1158
60. Zhao J.-P., He L., Jiang J., Tang Z., Cun L.-F., and Gong L.-Z. Tetrahedron Lett. 49 (2008) 3372-3375
61. Font D., Sayalero S., Bastero A., Jimeno C., and Pericas M.A. Org. Lett. 10 (2008) 337-340
62. Gandhi S., and Singh V.K. J. Org. Chem. 73 (2008) 9411-9416
63. For organocatalytical asymmetric aldol reaction in the presence of water, see:
64. Aratake S., Itoh T., Okano T., Nagae N., Sumiya T., Shoji M., and Hayashi Y. Chem.-Eur. J. 13 (2007) 10246-10256
65. Wang C., Jiang Y., Zhang X.-X., Huang Y., Li B.-G., and Zhang G.-L. Tetrahedron Lett. 48 (2007) 4281-4285
66. Lei M., Shi L., Li G., Chen S., Fang W., Ge Z., Cheng T., and Li R. Tetrahedron 63 (2007) 7892-7898
67. Gryko D., and Saletra W.J. Org. Biomol. Chem. 5 (2007) 2148-2153
68. Peng F.-Z., Shao Z.-H., Pu X.-W., and Zhang H.-B. Adv. Synth. Catal. 350 (2008) 2199-2204
69. Zu L., Xie H., Li H., Wang J., and Wang W. Org. Lett. 10 (2008) 1211-1214
70. Zhu M.-K., Xu X.-Y., and Gong L.-Z. Adv. Synth. Catal. 350 (2008) 1390-1396
71. Tzeng Z.-H., Chen H.-Y., Huang C.-T., and Chen K. Tetrahedron Lett. 49 (2008) 4134-4137
72. Camphor-based organocatalysts for various asymmetric transformations, see:
73. Aggarwal V.K., Hynd G., Picoul W., and Vasse J.-L. J. Am. Chem. Soc. 124 (2002) 9964-9965
74. Xu Z., Chen C., Xu J., Miao M., Yan W., and Wang R. Org. Lett. 6 (2004) 1193-1195
75. Rajaram S., and Sigman M.S. Org. Lett. 7 (2005) 5473-5475
76. Lemay M., and Ogilvie W.W. Org. Lett. 7 (2005) 4141-4144
77. Langlois Y., Petit A., Remy P., Scherrmann M.-C., and Kouklovsky C. Tetrahedron Lett. 49 (2008) 5576-5579
78. He H., Pei B.-J., Chou H.-H., Tian T., Chan W.-H., and Lee A.W.M. Org. Lett. 10 (2008) 2421-2424
79. For articles of chiral (thio)ureas in asymmetric synthesis, see:
80. Seayad J., and List B. Org. Biomol. Chem. 3 (2005) 719-724
81. Pihko P.M. Angew. Chem., Int. Ed. 43 (2004) 2062-2064
82. Connon S.J. Chem.-Eur. J. 12 (2006) 5418-5427 For selected references, see:
83. Raheem I.T., Thiara P.S., Peterson E.A., and Jacobsen E.N. J. Am. Chem. Soc. 129 (2007) 13404-13405
84. Wang J., Li H., Zu L., Jiang W., Xie H., Duan W., and Wang W. J. Am. Chem. Soc. 128 (2006) 12652-12653
85. Sigman M.S., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 4901-4902
86. Selected references for bifunctional organocatalysts, see:
87. Okino T., Hoashi Y., and Takemoto Y. J. Am. Chem. Soc. 125 (2003) 12672-12673
88. Liu T.-Y., Long J., Li B.-J., Jiang L., Li R., Wu Y., Ding L.-S., and Chen Y.-C. Org. Biomol. Chem. 4 (2006) 2097-2099
89. Andres J.M., Manzano R., and Pedrosa R. Chem.-Eur. J. 14 (2008) 5116-5119
90. Detailed X-ray crystallographic data is available from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK for organocatalyst 9 (CCDC No. 709277).
91. Sakthivel K., Notz W., Bui T., and Barbas III C.F. J. Am. Chem. Soc. 123 (2001) 5260-5267
92. Hoang L., Bahmanyar S., Houk K.N., and List B. J. Am. Chem. Soc. 125 (2003) 16-17
93. Bahmanyar S., Houk K.N., Martin H.J., and List B. J. Am. Chem. Soc. 125 (2003) 2475-2479