Dipeptide-catalyzed asymmetric aldol condensation of acetone with (N-alkylated) isatins

Journal of Organic Chemistry

Volumn 70, Issue 18, 2005, Pages 7418-7421

  Luppi, Gianluigi ^a   Cozzi, Pier Giorgio ^a   Monari, Magda ^a   Kaptein, Bernard ^b   Broxterman, Quirinus B ^b   Tomasini, Claudia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONDENSATION; POLYPEPTIDES; SPECTRUM ANALYSIS; X RAY DIFFRACTION;

CD SPECTRA ANALYSIS; ENANTIOSELECTIVITIES; ISATINS;

ACETONE;

DIPEPTIDE; ISATIN;

ALDOL REACTION; ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 24144493658     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050257l     Document Type: Article

References (25)

1. (a) Hajos, Z. G.; Parrish, D. R., J. Org. Chem. 1974, 39, 1615-162.
2. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497.
3. List, B. Acc. Chem. Res. 2004, 37, 548-557, and refs therein.
4. For a recent review, see: Dalko, P.; Moisan, P. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
5. Organocatalytic reactions mediated by oligopeptides, see: (a) Kofoed, J.; Nielsen, J.; Reymond, J.-L. Bio. Chem. Med. Lett. 2003, 13, 2445-2447.
6. (b) Jarvo, E.; Miller, S. J. Tetrahedron 2002, 58, 2481-2495.
7. (c) Shi, L.-X.; Sun, Q.; Ge, Z.-M.; Zhu, Y.-Q.; Cheng, T.-M.; Li, R.-T. Synlett 2004, 2215-2217.
8. (d) Tang, Z.; Yang, Z.-H.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Org. Lett. 2004, 6, 2285-2287.
9. (e) List, B.; Martin, H. J. Synlett 2003, 1901-1902.
10. For the racemic aldol condensation of isatins with methylketones, see: (a) Kawasaki, T.; Nagaoka, M.; Satoh, T.; Okamoto, A.; Ukon, R.; Ogawa, A. Tetrahedron 2004, 60, 3493-3503.
11. (b) Garner, S. J.; da Silva, R. B.; Pinto, A. C. Tetrahedron 2002, 58, 8399-8412.
12. (c) Beccalli, E. M.; Marchesini A.; Pilati, T. J. Chem. Soc., Perkin Trans, 1 1994, 579-587.
13. For the use of prolinamide as a catalyst, see: (a) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. PNAS 2004, 101, 5755-5760.
14. (b) Marigo, M.; Bachmann, S.; Halland, N.; Braunton, A. Jörgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 5507-5510.
15. (c) Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817-2820.
16. (a) Formaggio, F.; Moretto, V.; Crisma, M.; Toniolo, C.; Kaptein, B.; Broxterman, Q. B. J. Peptide Res. 2004, 63, 161-170.
17. (b) Kruizinga, W. H.; Bolster, J.; Kellogg, R. M.; Kamphuis, J.; Boesten, W. H. J.; Meijer E. M.; Sehoemaker H. E. J. Org. Chem. 1988, 53, 1826-1827.
18. (c) Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Peters, P. J. H.; Schoemaker H. E.; Kamphuis, J. Tetrahedron: Asymmetry 1993, 4, 1113-1116.
19. (a) Boesten, W. H. J.; Moody, H. M.; Kaptein, B.; Seerden, J. P. G.; van der Sluis, M.; de Lange, B. (DSM). PCT Pat. Appl. WO 01/42173.
20. (b) Broxterman, Q. B.; Kaptein, B.; Kierkels J. G. T.; Milcent, T. J. A. (DSM) Eur. Pat. Appl. No. 04075597.7 (patent pending).
21. See for example: (a) Stefani, R.; Cesare, V. J. Chromat. A. 1998, 813, 79-84.
22. (b) Loža, E.; Loïa D.; Íemme, A.; Freimanis, J. J. Chromatogr. A. 1995, 708, 231-243.
23. Takayama, H.; Shimizu, T.; Sada, H.; Harada, Y.; Kitajima, M.; Aimi, N. Tetrahedron 1999, 55, 6841-6846.
24. Azizian, J.; Fallah-Bagher-Shaidaci, H.; Kefayati, H. Synth. Commun. 2003, 33, 789-793.
25. Krishna, C.; Kundu, A. K.; Pranab, C. J. Chem. Res., Synop. 1996, 10, 460-461.