Synthesis of 3-oxo-2,3-dihydropyrrole amino acids as chiral dipeptidomimics

Synthesis

Volumn , Issue 16, 2006, Pages 2719-2724

  Maity, Prantik ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

3 oxo 2,3 dihydropyrrole; Allylations; Amino acids; Catalysis; Palladium; Pyrroles

Indexed keywords

ALDEHYDES; CATALYSIS; ESTERS; PALLADIUM; SYNTHESIS (CHEMICAL);

ALLYLATIONS; ENANTIOSELECTIVE CONVERSION; PYRROLES;

AMINO ACIDS;

1 TERT BUTYL 2 ETHYL 2 ALLYL 5 (TERT BUTOXYCARBONYLAMINOMETHYL) 4 METHYL 3 OXO 2,3 DIHYDROPYRROLE 1,2 DICARBOXYLATE; 1 TERT BUTYL 2 ETHYL 2 ALLYL 5 [(2 TERT BUTOXYCARBONYLAMINO 3 PHENYLPROPINOYLAMINO)METHYL] 4 METHYL 3 OXO 2,3 DIHYDRO PYRROLE 1,2 DICARBOXYLATE; 1 TERT BUTYL 2 ETHYL 3 BENZYLOXY 5 (TERT BUTOXYCARBONYLAMINOMETHYL) 4 METHYLPYRROLE 1,2 DICARBOXYLATE; 1 TERT BUTYL 2 ETHYL 3 BENZYLOXY 5 FORMYL 4 METHYLPYRROLE 1,3 DICARBOXLATE; 1 TERT BUTYL 2 ETHYL 5 (TERT BUTOXYCARBONYLAMINOMETHYL) 2 CARBOXYETHYL 4 METHYL 3 OXO 2,3 DIHYDROPYRROLE 1,2 DICARBOXYLATE; 1 TERT BUTYL 2 ETHYL 5 (TERT BUTOXYCARBONYLAMINOMETHYL) 4 METHYL 3 OXO 2 (2 OXOETHYL) 2,3 DIHYDROPYRROLE 1,2 DICARBOXYLATE; 1 TERT BUTYL 2 ETHYL 5 (TERT BUTOXYCARBONYLAMINOMETHYL) 4 METHYL 3 OXO 2,3 DIHYDROPYRROLE 1,2 DICARBOXYLATE; 2 CARBOXY 3 HYDROXY PYRROLE; 3 OXO 2,3 DIHYDROPYRROLE 2 ALLYL 2 CARBOXYLATE; 3 OXO 2,3 DIHYDROPYRROLE AMINO ACID DERIVATIVE; AMINO ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIPEPTIDE; ETHYL 2 ALLYL 5 (TERT BUTOXYCARBONYLAMINOMETHYL) 4 METHYL 3 OXO 2,3 DIHYDRO 1H PYRROLE 2 CARBOXYLATE; ETHYL 3 BENZYLOXY 4 METHYL 1H PYRROLE 2 CARBOXYLATE; ETHYL 3 BENZYLOXY 5 (TERT BUTOXYCARBONYLAMINOMETHYL) 4 METHYL 1H PYRROLE 2 CARBOXYLATE; ETHYL 3 BENZYLOXY 5 FORMYL 4 METHYL 1H PYRROLE 2 CARBOXYLATE; ETHYL 5 (TERT BUTOXYCARBONYLAMINOMETHYL) 3 HYDROXY 4 METHYL 1 H PYRROLE 2 CARBOXYLATE; PALLADIUM; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 33748304098     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942497     Document Type: Article

References (22)

1. Smith, A. B. III; Akaishi, R.; Jones, D. R.; Keenan, T. P.; Guzman, M. C.; Holcomb, R. C.; Hirschmann, R.; Wood, J. L.; Hirschmann, R.; Holloway, M. K. Biopolymers 1995, 37, 2953.
2. Smith, A. B. III; Hirschmann, R.; Pasternak, A.; Guzman, M. C.; Yokoyama, A.; Sprengeler, P. A.; Darke, P. L.; Emini, E. A.; Schleif, W. A. J. Am. Chem. Soc. 1995, 117, 11113.
3. Smith, A. B. III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holocomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947.
4. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
5. Bittermann, H.; Gmeiner, P. J. Org. Chem. 2006, 71, 97.
6. (a) Bonauer, C.; Zabel, M.; König, B. Org. Lett. 2004, 6, 1349.
7. (b) Kruppa, M.; Bonauer, C.; Michlová, V.; König, B. J. Org. Chem. 2005, 70, 5305.
8. (c) Bonauer, C.; König, B. Synthesis 2005, 2367.
9. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327.
10. The compound was prepared according to: Bonauer, C. Dissertation; Universität Regensburg: Germany, 2004.
11. Momose, T.; Tanaka, T.; Yokota, T.; Nagamoto, N.; Yamada, K. Chem. Pharm. Bull. 1978, 26, 3521.
12. Trost, B. M.; Schroeder, G. M. Chem. Eur. J. 2005, 11, 174.
13. For examples of non-enantioselective stoichiometric related reactions, see: (a) Beyer, M.; Ghaffari-Tabrizi, R.; Jung, M.; Margaretha, P. Helv. Chim. Acta 1984, 67, 1535.
14. (b) Plieninger, H.; Herzog, H. Monatsh. Chem. 1967, 98, 807.
15. (a) Drew, M. G. B.; George, A. V.; Isaacs, N. S.; Rzepa, H. S. J. Chem. Soc., Perkin Trans. 1 1985, 1277.
16. (b) Bennes, R.; Babiloni, M. S.; Hayes, W.; Philip, D. Tetrahedron Lett. 2001, 42, 2377.
17. (c) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
18. Genin, M. L.; Johnson, R. L. J. Am. Chem. Soc. 1992, l14, 8778.
19. Zhang, R.; Mamai, A.; Madalengoitia, J. S. J. Org. Chem. 1999, 64, 547.
20. 3J) between NH of the peptide bond and the α-CH shows a value of 5.9 Hz which indicates free rotation of the 3-oxo-2,3-dihydropyrrole moieties around the connecting single bond.
21. (a) Trost, B. M.; Schroeder, G. M.; Kristensen, J. Angew. Chem. Int Ed. 2002, 41, 3429.
22. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545.