Novel enantiocontrol system with aminoacyl derivatives of glucoside as enamine-based organocatalysts for aldol reaction in aqueous media

Tetrahedron Letters

Volumn 48, Issue 30, 2007, Pages 5213-5217

  Tsutsui, Ayumi ^a   Takeda, Hiroshi ^a   Kimura, Masaya ^a   Fujimoto, Takashi ^a   Machinami, Tomoya ^a  

^a MEISEI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROBENZALDEHYDE; ACETONE; AMIDE; AMINO ACID; BENZALDEHYDE DERIVATIVE; CARBOHYDRATE; ENAMINE; GLUCOPYRANOSIDE; GLUCOSIDE; HYDROXYL GROUP; NITRO DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 34250878930     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.139     Document Type: Article

References (21)

1. Sakthivel K., Notz W., Bui T., and Barbas III C.F. J. Am. Chem. Soc. 122 (2001) 5260-5267
2. List B., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 122 (2000) 2395-2396
3. Lindstrom U.M. Chem. Rev. 102 (2002) 2751-2772
4. Dickerson T.J., and Janda K.D. J. Am. Chem. Soc. 124 (2002) 3220-3221
5. Dickerson T.J., Lovell T., Meijler M.M., Noodleman L., and Janda K.D. J. Org. Chem. 69 (2004) 6603-6609
6. Zhu X., Tanaka F., Hu Y., Heine A., Fuller R., Zhing G., Olson A.J., Lerner R.A., Barbas III C.F., and Wilson I.A. J. Mol. Biol. 343 (2004) 1269-1280 and references cited therein
7. Wagner J., Lehner R.A., and Barbas III C.F. Science 278 (1997) 2085-2092
8. Barbas III C.F., Heine A., Zhong G., Hoffmann T., Gramatikova S., Björnestedt G., List B., Anderson J., Stura E.A., Wilson I.A., and Lzerner R.A. Science 278 (1997) 2085-2092
9. Hoffmann T., Zhong G., List B., Shabat D., Anderson J., Gramatikova S., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 120 (1998) 2768-2779
10. Cordova A., Notz W., and Barbas III C.F. Chem. Commun. (2002) 3024-3025
11. 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
12. Hayashi Y., Sumiya T., Takahashi J., Gotoh H., Urushima T., and Shoji M. Angew. Chem., Int. Ed. 45 (2006) 958-961
13. +, 292.13963; found, 292.14152.
14. +, 307.18691; found, 307.18318.
15. Machinami T., Iibuchi N., Nomura T., Mitsumori T., Suami T., and Hough L. J. Carbohydr. Chem. 21 (2002) 131-142
16. +, 308.17093; found, 308.17381.
17. In the preliminary experiments, the enantioselectivities, 17% ee (R) for l-leucine and 12% ee (R) for l-tert-leucine, were detected in the reaction of acetone with 4-nitrobenzaldehyde in acetone-water (4:5) using amino acid alone. In acetone-water (20:1) media, 10% yield with 44% ee (R) was detected for l-tert-leucine.
18. In the reaction of acetone with 4-nitrobenzaldehyde in acetone-water (4:5), methyl 2-(l-phenylalanyl)oxy-α-d-glucopyranoside led to 18% ee (S), whereas 13% ee (R) was detected for the reaction with l-phenylalanine alone.
19. The enantioreversal control with l-proline related catalyst only reported for Zn-proline complex, although the complex represents the model for class II aldolase. Darbe T., and Machuqueiro M. Chem. Commun. (2003) 1090-1091
20. Kofoed J., Darbre T., and Reymond J.-L. Chem. Commun. (2006) 1482-1484
21. Kofoed J., Nielsen J., and Reymond J.-L. Bioorg. Med. Chem. Lett. 13 (2003) 2445-2447 and references cited therein