Density functional theory study of the stereoselectivity in small peptide-catalyzed intermolecular aldol reactions

Tetrahedron Asymmetry

Volumn 19, Issue 13, 2008, Pages 1617-1621

  Hammar, Peter ^a   Córdova, Armando ^b   Himo, Fahmi ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BENZALDEHYDE; CYCLOHEXANONE; CYCLOHEXENE DERIVATIVE; DIPEPTIDE; PEPTIDE;

ALDOL REACTION; ARTICLE; CATALYSIS; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; HYDROGEN BOND; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 48949114919     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.06.014     Document Type: Article

References (73)

1. Trost B.M., Fleming I., and Heathcock C.-H. Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford
2. In: Mahrwald R. (Ed). Modern Aldol Reactions Vols. 1 & 2 (2004), Wiley-VCH, Weinheim
3. Carreira E.M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis (1999), Springer, Heidelberg
4. Johnson J.S., and Evans D.A. Acc. Chem. Res. 33 (2000) 325
5. Palomo C., Oiarbide M., and García J.M. Chem. Soc. Rev. 33 (2004) 65
6. Fessner W.-D. In: Patel R.N. (Ed). Stereoselective Biocatalysis (2000), Marcel Dekker, New York 239
7. Machajewski T.D., and Wong C.-H. Angew. Chem., Int. Ed. 39 (2000) 1352
8. Heine A., DeSantis G., Luz J.G., Mitchell M., Wong C.-H., and Wilson I.A. Science 294 (2001) 369
9. Pizzarello S., and Weber A.L. Science 303 (2004) 1151
10. Córdova A., Ibrahem I., Casas J., Sundén H., Engqvist M., and Reyes E. Chem. Eur. J. 11 (2005) 4772
11. Córdova A., Engqvist M., Ibrahem I., Casas J., and Sundén H. Chem. Commun. (2005) 2047
12. Kofoed J., Machuqueiro M., Reymond J.-L., and Darbre T. Chem. Commun. 26 (2004) 1540
13. Hajos, Z. G.; Parrish, D. R. German Patent DE 2102623, July 29, 1971.
14. Hajos Z.G., and Parrish D.R. J. Org. Chem. 39 (1974) 1615
15. Eder, U.; Sauer, G.; Wiechert, R. German Patent DE 2014757, October 7, 1971.
16. Eder U., Sauer G., and Wiechert R. Angew. Chem., Int. Ed. Engl. 10 (1971) 496
17. Danishefsky S., and Cain P. J. Am. Chem. Soc. 97 (1975) 5282
18. Shimizu I., Naito Y., and Tsuji J. Tetrahedron Lett. 21 (1980) 4975
19. Hagiwara H., and Uda H. J. Org. Chem. 53 (1988) 2308
20. Corey E.J., and Virgil S.C. J. Am. Chem. Soc. 112 (1990) 6429
21. List B., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 122 (2000) 2395
22. Notz W., and List B. J. Am. Chem. Soc. 122 (2000) 7386
23. Mukherjee S., Yang J.W., Hoffmann S., and List B. Chem. Rev. 107 (2007) 5471
24. For selected early contributions on the proline-catalyzed intermolecular aldol reaction see reviews:. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 40 (2001) 3726
25. List B. Tetrahedron 58 (2002) 5573
26. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138
27. See also some selected early papers:. List B., Pojarliev P., and Castello C. Org. Lett. 3 (2001) 573
28. Sakthivel K.S., Notz W., Bui T., and Barbas III C.F. J. Am. Chem. Soc. 123 (2001) 5260
29. Córdova A., Notz W., and Barbas III C.F. Chem. Commun. 67 (2002) 3034
30. Córdova A., Notz W., and Barbas III C.F. J. Org. Chem. 67 (2002) 301
31. Northrup A.B., and MacMillan D.W.C. J. Am. Chem. Soc. 124 (2002) 6798
32. Bøgevig A., Kumaragurubaran N., and Jørgensen K.A. Chem. Commun. (2002) 620
33. List B., Hoang L., and Martin H.J. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5839
34. Nyberg A.I., Usano A., and Pihko P. Synlett (2004) 1891
35. For examples of N-terminal prolyl peptide-catalyzed asymmetric aldol reactions see:. Kofoed J., Nielsen J., and Reymend J.-L. Biorg. Med. Chem. Lett. 13 (2003) 2445
36. Martin H.J., and List B. Synlett (2003) 1901
37. Tang Z., Yang Z.-H., Cun L.-F., Gong L.-Z., Mi A.-Q., and Jiang Y.-Z. Org. Lett. 6 (2004) 2285
38. Krattiger P., Kovasy R., Revell J.D., Ivan S., and Wennemers H. Org. Lett. 7 (2005) 1101
39. For an excellent review on the use of peptides in asymmetric catalysis see:. Davie E.A.C., Mennen S.M., Xu Y., and Miller S.J. Chem. Rev. 107 (2007) 5759
40. Bahmanyar S., and Houk K.N. J. Am. Chem. Soc. 123 (2001) 12911
41. Bahmanyar S., and Houk K.N. J. Am. Chem. Soc. 123 (2001) 11273
42. Bahmanyar S., Houk K.N., Martin H.J., and List B. J. Am. Chem. Soc. 125 (2003) 2475
43. Hoang L., Bahmanyar S., Houk K.N., and List B. J. Am. Chem. Soc. 125 (2003) 16
44. Clemente F.R., and Houk K.N. Angew. Chem., Int. Ed. 43 (2004) 5766
45. Rankin K.N., Gauld J.W., and Boyd R. J. Phys. Chem. A 106 (2002) 5155
46. Alleman C., Gordillo R., Clemente F.R., Cheong P.H.-Y., and Houk K.N. Acc. Chem. Res. 37 (2004) 558
47. Fan J.-F., Wu L.-F., and Tao F.-M. Int. J. Quant. Chem. 108 (2008) 66
48. For DFT calculations of the acyclic amino acid-catalyzed intramolecular aldol reaction see:. Clemente F.R., and Houk K.N. J. Am. Chem. Soc. 127 (2005) 11294
49. Seebach D., Beck A.K., Badine D.M., Limbach M., Eschenmoser A., Treasurywala A.M., Hobi R., Prikoszovich W., and Linder B. Helv. Chem. Acta 90 (2007) 425
50. Córdova A., Zou W., Ibrahem I., Reyes E., Engqvist M., and Liao W.-W. Chem. Commun. (2005) 3586
51. Bassan A., Zou W., Reyes E., Himo F., and Córdova A. Angew. Chem., Int. Ed. 44 (2005) 7028
52. For selected examples of highly enantioselective intermolecular aldol reactions catalyzed by amino acids with a primary amine functionality see:. Jiang Z., Liang Z., Wu X., and Lu Y. Chem. Commun. (2006) 2801
53. Deng D.-S., and Cai J. Helv. Chim. Acta 90 (2007) 119
54. Wu X., Jian Z., Shen H.-M., and Lu Y. Adv. Synth. Catal. 349 (2007) 812
55. Ramasastry S.S.V., Zhang H., Tanaka F., and Barbas III C.F. .J. Am. Chem. Soc. 129 (2007) 288
56. Ramasastry S.S.V., Albertshofer K., Utsumi N., Tanaka F., and Barbas III C.F. Angew. Chem., Int. Ed. 46 (2007) 5572
57. See also:. Amedjkouh M. Tetrahedron: Asymmetry 16 (2005) 1411
58. Limbach M. Tetrahedron Lett. 47 (2006) 3843
59. Zou W., Ibrahem I., Dziedzic P., Sundén H., and Córdova A. Chem. Commun. (2005) 4946
60. Dziedzic P., Zou W., Hafren J., and Córdova A. Org. Biol. Chem. 4 (2006) 38
61. Córdova A., Zou W., Dziedzic P., Ibrahem I., Reyes E., and Xu Y. Chem. Eur. J. 12 (2006) 5383
62. Córdova A., Zou W., Dziedzic P., Ibrahem I., Reyes E., and Xu Y. Chem. Eur. J. 12 (2006) 5175
63. Weber A.L., and Pizzarrello S. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 12713
64. Tsogoeva S., and Wei S. Tetrahedron: Asymmetry 16 (2005) 1947
65. Carrea G., Ottolina G., Lazcano A., Pironti V., and Colonna S. Tetrahedron: Asymmetry 18 (2007) 1265
66. Ledl F., and Schleicher E. Angew. Chem., Int. Ed. 29 (1990) 565
67. Nursten H. The Maillard Reaction, Chemistry, Biochemistry and Implications (2005), Royal Society of Chemistry, Cambridge
68. Steinhart H. Angew. Chem., Int. Ed. 44 (1999) 7503
69. Somoza V. Mol. Nutr. Food Res. 49 (2005) 663
70. Baynes J.W., and Monnier V.M. The Maillard Reaction in Ageing. Diabetes and Nutrition; Progress in Clinical and Biological Research Vol. 304 (1989), Alan R. Liss, New York
71. Becke A.D. J. Chem. Phys. 98 (1993) 5648
72. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. gaussian 03, Revision D.01 (2004), Gaussian, Wallingford, CT
73. Barone V., and Cossi M. J. Phys. Chem. A 102 (1998) 1995