Three-component Staudinger-type stereoselective synthesis of C-glycosyl-β-lactams and their use as precursors for C-glycosyl isoserines and dipeptides. A polymer-assisted solution-phase approach

Advanced Synthesis and Catalysis

Volumn 346, Issue 11, 2004, Pages 1355-1360

  Dondoni, Alessandro ^a   Massi, Alessandro ^a   Sabbatini, Simona ^a   Bertolasi, Valerio ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

lactams; 2+2 cycloaddition; C glycosides; C glycosyl amino acids; Multicomponent reaction

Indexed keywords

BETA LACTAM DERIVATIVE; DIPEPTIDE DERIVATIVE; GLYCOSIDE; ISOSERINE; METHANOL; PHENYLALANINE METHYL ESTER; POLYMER; RESIN;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS; STAUDINGER REACTION; STEREOCHEMISTRY;

EID: 7044269424     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404100     Document Type: Article

References (28)

1. a) A. Dondoni, A. Massi, S. Sabbatini, V. Bertolasi, J. Org. Chem. 2002, 67, 6979-6994;
2. b) A. Dondoni, A. Massi, E. Minghini, V. Bertolasi, Helv. Chim. Acta 2002, 85, 3331-3348;
3. c) A. Dondoni, A. Massi, E. Minghini, S. Sabbatini, V. Bertolasi, J. Org. Chem. 2003, 68, 6172-6183;
4. d) A. Dondoni, A. Massi, Mol. Diversity 2003, 6, 261-270;
5. e) A. Dondoni, A. Massi, E. Minghini, V. Bertolasi, Tetrahedron 2004, 60, 2311-2326.
6. For reviews, see: a) The Organic Chemistry of β-Lactams, (Ed.: G. I. Georg), VCH, New York, 1993; b) M. Kidwai, P. Sapra, K. R. Bhushan, Curr. Med. Chem. 1999, 6, 195-215.
7. For reviews, see: a) The Organic Chemistry of β-Lactams, (Ed.: G. I. Georg), VCH, New York, 1993; b) M. Kidwai, P. Sapra, K. R. Bhushan, Curr. Med. Chem. 1999, 6, 195-215.
8. For several articles devoted to β-lactam chemistry and synthesis, see the thematic issue of Tetrahedron 2000, 56, 5553-5742.
9. M. Carina, L. Delpiccolo, M. A. Fraga, E. G. Mata, J. Comb. Chem. 2003, 5, 208-210, and references cited therein.
10. a) I. Ojima, in: The Organic Chemistry of β-Lactams, (Ed.: G. I. Georg), VCH, New York, 1993, pp. 197-255;
11. b) I. Ojima, S. Lin, J. Org. Chem. 1998, 63, 224-225, and references cited therein.
12. The stereoselective synthesis of non-anomeric sugar β-lactams via [2+2] cycloaddition of achiral ketenes to chiral imines derived from cyclic dialdoses was reported earlier by Palomo and co-workers: C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. I. Miranda, A. Linden, J. Org. Chem. 1998, 63, 5838-5846; and more recently by Indian researchers: M. Arun, S. N. Joshi, V. G. Puranik, B. M. Bhawal, A. R. A. S. Deshmukh, Tetrahedron 2003, 59, 2309-2316.
13. The stereoselective synthesis of non-anomeric sugar β-lactams via [2+2] cycloaddition of achiral ketenes to chiral imines derived from cyclic dialdoses was reported earlier by Palomo and co-workers: C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. I. Miranda, A. Linden, J. Org. Chem. 1998, 63, 5838-5846; and more recently by Indian researchers: M. Arun, S. N. Joshi, V. G. Puranik, B. M. Bhawal, A. R. A. S. Deshmukh, Tetrahedron 2003, 59, 2309-2316.
14. For reviews, see: a) G. I. Georg, V. T. Ravikumar, in: The Organic Chemistry of β-Lactams, (G. I. Georg), VCH, New York, 1993, pp. 295-368; b) C. Palomo, J. M. Aizpurua, I. Ganboa, M. Oiarbide, Eur. J. Org. Chem. 1999, 3223-3235.
15. For reviews, see: a) G. I. Georg, V. T. Ravikumar, in: The Organic Chemistry of β-Lactams, (G. I. Georg), VCH, New York, 1993, pp. 295-368; b) C. Palomo, J. M. Aizpurua, I. Ganboa, M. Oiarbide, Eur. J. Org. Chem. 1999, 3223-3235.
16. a) A. Dondoni, M.-C Scherrmann, J. Org. Chem. 1994, 59, 6404-6412;
17. b) A. Dondoni, Pure Appl. Chem. 2000, 72, 1577-1588;
18. c) A. Dondoni, P. Formaglio, A. Marra, A. Massi, Tetrahedron 2001, 57, 7719-7727.
19. In general an excess of aldehyde is employed for the in situ generation of the imine. These conditions are used to avoid the presence of unreacted amine which subtracts part of the ketene.
20. For a fully automatable procedure, the ketene generation was also carried out by using the highly basic (but quite expensive) BEMP resin (polymer-bound triaminophosphonamide imine) that removes the trialkylammonium salt by-products and therefore simplifies considerably the work-up procedure. Full details of this methodology will be reported in a forthcoming paper. For the earlier use of the BEMP resin for ketene generation, see: A. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris, T. Lectka, J. Am. Chem. Soc. 2002, 124, 6626-6635.
21. A. Dondoni, F. Junquera, F. L. Merchan, P. Merino, M.-C. Scherrmann, T. Tejero, J. Org. Chem. 1997, 62, 5484-5496.
22. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 235150. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax.: (internat.) +44 1223/336-033; e-mail: deposit@ccdc.cam.ac.uk]. For enquires contact V. B. at the indicated address or by e-mail.
23. The ease of removal of all protective groups from the β-lactam ring and sugar residue by CAN oxidation and hydrogenolysis was demonstrated in compounds (3R,4S)-3b and (3R,4S)-4c.
24. C. Palomo, J. M. Aizpurua, C. Cuevas, A. Mielgo, R. Galarza, Tetrahedron Lett. 1995, 36, 9027-9030.
25. a) I. Ojima, C. M. Sun, Y. H. Park, J. Org. Chem. 1994, 59, 1249-1250;
26. b) C. Palomo, J. M. Aizpurua, C. Cuevas, J. Chem. Soc. Chem. Commun. 1994, 1957-1958.
27. a) P. M. St. Hilaire, M. Meldal, Angew. Chem. Int. Ed. 2000, 39, 1162-1179;
28. b) A. Barkley, P. Arya, Chem. Eur. J. 2001, 7, 555-563.