The mimic of type II aldolases chemistry: Asymmetric synthesis of β-Hydroxy Ketones by Direct Aldol Reaction: Research Letter

Chemical Biology and Drug Design

Volumn 76, Issue 2, 2010, Pages 181-186

  Lu, Zhijin ^a   Mei, Haibo ^a   Han, Jianlin ^a   Pan, Yi ^a,b  

^a NANJING UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

aldol reaction; chiral prolinamides; zinc triflate; hydroxy ketone

Indexed keywords

ALDEHYDE; BENZALDEHYDE DERIVATIVE; BETA HYDROXY KETONE; CYCLOHEXANONE; FRUCTOSE BISPHOSPHATE ALDOLASE; KETONE DERIVATIVE; UNCLASSIFIED DRUG; 1,2-DIAMINOBENZENE; 4-NITROBENZALDEHYDE; CYCLOHEXANONE DERIVATIVE; KETONE; MESYLIC ACID DERIVATIVE; PHENYLENEDIAMINE DERIVATIVE; PROLINAMIDE; PROLINE; TRIFLUOROMETHANESULFONIC ACID;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BENZALDEHYDES; CATALYSIS; CYCLOHEXANONES; FRUCTOSE-BISPHOSPHATE ALDOLASE; KETONES; MESYLATES; PHENYLENEDIAMINES; PROLINE; STEREOISOMERISM;

EID: 77954366502     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2010.00998.x     Document Type: Article

References (42)

1. Heathcock C.H. (1991) In : Trost B.M., Fleming I., Heathcock C.H., editors. Comprehensive Organic Synthesis, Vol. 2.
2. Carreira E.M. (1999) In : Jacobsen E.N., Pfaltz A., Yamamoto H., editors. Comprehensive Asymmetric Catalysis, Vol. 3, Chapter 29.1.
3. Shibasaki M., Yoshikawa N., Matsunaga S. (2003) In : Jacobsen E.N., Pfaltz A., Yamamoto H., editors. Comprehensive Asymmetric Catalysis, Supp. 1, Chapter 29.4.
4. Machajewski T.D., Wong C.H. (2000) The catalytic asymmetric aldol reaction. Angew Chem Int Ed 39 : 1352 1374.
5. Heathcock H. (1984) In : Morrison J.D., editor. Asymmetric Synthesis, Vol. 3, Chapter 2.
6. Masamune S., Choy W., Petersen J.S., Sita L.R. (1985) Double asymmetric synthesis and a new strategy for stereochemical control in organic synthesis. Angew Chem Int Ed Engl 24 : 1 30.
7. West L.M., Northcote P.T. (2000) Peloruside A: a potent cytotoxic macrolide isolated from the new Zealand marine sponge mycale sp. J Org Chem 65 : 445 449.
8. Höfle G., Bedorf N., Steinmetz H., Schomburg D., Gerth K., Reichenbach H. (1996) Epothilone A and B-novel 16-membered macrolides with cytotoxic activity: Isolation, crystal structure, and conformation in solution. Angew Chem Int Ed Engl 35 : 1567 1569.
9. Ghosh A.K., Kass J., Anderson D.D., Xu X.M., Marian C. (2008) L-selectride-mediated highly diastereoselective asymmetric reductive aldol reaction: access to an important subunit for bioactive molecules. Org Lett 10 : 4811 4814.
10. Raghavan S., Rathore K. (2009) Asymmetric synthesis of (-)-tetrahydrolipstatin. Tetrahedron 65 : 10083 10092.
11. Dias L.C., Goncalves C.D.C.S. (2008) Total synthesis of (-)-basiliskamide B. Adv Synth Catal 350 : 1017 1021.
12. Malathong V., Rychnovsky S.D. (2009) Polyol synthesis with β-oxyanionic alkyllithium reagents: syntheses of aculeatins A, B, and D. Org Lett 11 : 4220 4223.
13. Magee T.V., Ripp S.L., Flanagan M.E. (2009) Discovery of azetidinyl ketolides for the treatment of susceptible and multidrug resistant community-acquired respiratory tract infections. J Med Chem 52 : 7446 7457.
14. Matsukawa Y., Isobe M., Kotsuki H., Ichikawa Y. (2005) Synthesis of (+)-conagenin. J Org Chem 70 : 5339 5341.
15. Aratake S., Itoh T., Okano T., Usui T., Shoji M., Hayashi Y. (2007) Small organic molecule in enantioselective, direct aldol reaction "in water". Chem Commun 2524 2526.
16. Gruttadauria M., Giacalone F., Marculescu A.M., Noto R. (2008) Novel prolinamide-supported polystyrene as highly stereoselective and recyclable organocatalyst for the aldol reaction. Adv Synth Catal 350 : 1397 1405.
17. Zu L.S., Wang J., Li H., Wang W. (2006) A recyclable fluorous (S)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water. Org Lett 8 : 3077 3079.
18. Zu L., Xie H., Li H., Wang J., Wang W. (2008) Highly enantioselective aldol reactions catalyzed by a recyclable fluorous (S) pyrrolidine sulfonamide on water. Org Lett 10 : 1211 1214.
19. Guizzetti S., Benaglia M., Raimondi L., Celentano G. (2007) Enantioselective direct aldol reaction "on water" promoted by chiral organic catalysts. Org Lett 9 : 1247 1250.
20. Zhu M., Xu X., Gong L. (2008) Organocatalytic asymmetric syn-aldol reactions of aldehydes with long-chain aliphatic ketones on water and with dihydroxyacetone in organic solvents. Adv Synth Catal 350 : 1390 1396.
21. Chimni S.S., Singh S., Mahajan D. (2008) Protonated (S)-prolinamide derivatives-water compatible organocatalysts for direct asymmetric aldol reaction. Tetrahedron Asymmetry 19 : 2276 2284.
22. Zhang S.P., Fu X.K., Fu S.D. (2009) Rationally designed 4-phenoxy substituted prolinamide phenols organocatalyst for the direct aldol reaction in water. Tetrahedron Lett 50 : 1173 1176.
23. Chimni S.S., Singh S., Kumar A. (2009) The pH of the reaction controls the stereoselectivity of organocatalyzed direct aldol reactions in water. Tetrahedron Asymmetry 20 : 1722 1724.
24. Trost B.M., Fettes A., Shireman B.T. (2004) Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction. J Am Chem Soc 126 : 2660 2661.
25. Trost B.M., Yeh V.S.C. (2002) A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction. Angew Chem Int Ed Engl 41 : 861 863.
26. Yamada Y.M.A., Yoshikawa N., Sasai H., Shibasaki M. (1997) Direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones. Angew Chem Int Ed Engl 36 : 1871 1873.
27. Yoshikawa N., Yamada Y.M.A., Das J., Sasai H., Shibasaki M. (1999) Direct catalytic asymmetric aldol reaction. J Am Chem Soc 121 : 4168 4178.
28. List B., Lerner R.A., Barbas C.F. III. (2000) Proline-catalyzed direct asymmetric aldol reactions. J Am Chem Soc 122 : 2395 2396.
29. Mukherjee S., Yang J.W., Hoffmann S., List B. (2007) Asymmetric enamine catalysis. Chem Rev 107 : 5471 5569.
30. Dalko P.I., Moisan L. (2001) Enantioselective organocatalysis. Angew Chem Int Ed Engl 40 : 3726 3748.
31. Dalko P.I., Moisan L. (2004) In the golden age of organocatalysis. Angew Chem Int Ed 43 : 5138 5175.
32. Northrup A.B., MacMillan D.W.C. (2002) The first direct and enantioselective cross-aldol reaction of aldehydes. J Am Chem Soc 124 : 6798 6799.
33. Paradowska J., Stodulski M., Mlynarskia J. (2007) Direct catalytic asymmetric aldol reactions assisted by zinc complex in the presence of water. Adv Synth Catal 349 : 1041 1046.
34. Darbe T., Machuqueiro M. (2003) Zn-proline catalyzed direct aldol reaction in aqueous media. Chem Commun 1090 1091.
35. Kofoed J., Machuqueiro M., Reymond J.L., Darbre T. (2004) Zinc-proline catalyzed pathway for the formation of sugars. Chem Commun 1540 1541.
36. Itoh S., Kitamura M., Yamada Y., Aoki S. (2009) Chiral catalysts dually functionalized with amino acid and Zn2+ complex components for enantioselective direct aldol reactions inspired by natural aldolases: design, synthesis, complexation properties, catalytic activities, and mechanistic study. Chem Eur J 15 : 10570 10584.
37. Mlynarski J., Paradowska J. (2008) Catalytic asymmetric aldol reactions in aqueous media. Chem Soc Rev 37 : 1502 1511.
38. Paradowska J., Stodulski M., Mlynarski J. (2009) Catalysts based on amino acids for asymmetric reactions in water. Angew Chem Int Ed 48 : 4288 4297.
39. Kofoed J., Darbre T., Reymond J.L. (2006) Dual mechanism of zinc-proline catalyzed aldol reactions in water. Chem Commun 1482 1484.
40. Fernandez-Lopez R., Kofoed J., Machuqueiro M., Darbre T. (2005) A selective direct aldol reaction I aqueous media catalyzed by zinc-proline. Eur J Org Chem 5268 5276.
41. Luo S.Z., Xu H., Li J.Y., Zhang L., Mi X.L., Zheng X.X., Cheng J.P. (2007) Facile evolution of asymmetric organocatalysts in water assisted by surfactant Brønsted acids. Tetrahedron 63 : 11307 11314.
42. Tang Z., Jiang F., Cui X., Gong L.Z., Mi A.Q., Jiang Y.Z., Wu Y.D. (2004) Enantioselective direct aldol reactions catalyzed by L-prolinamide derivatives. Proc Natl Acad Sci U S A 101 : 5755 5760.