A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent ugi reaction

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 575-579

  Basso, Andrea ^a   Banfi, Luca ^a   Riva, Renata ^a   Guanti, Giuseppe ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; DERIVATIVES; REACTION KINETICS; STEREOCHEMISTRY;

CHIRAL AUXILIARY; ENANTIOMERS; UGI MULTICOMPONENT REACTION;

AROMATIC HYDROCARBONS;

ACID ANHYDRIDE; ALDEHYDE; AMINO ACID DERIVATIVE; CARBOXYLIC ACID; CYANIDE; ESTER; N BENZYL BETA AMINO ACID; PHENETHYLAMINE; QUINIDINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BENZYLATION; CHEMICAL REACTION; CHIRALITY; DEPROTECTION REACTION; DIELS ALDER REACTION; ENANTIOMER; EPIMERIZATION; RACEMIZATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

ALDEHYDES; AMINO ACIDS; BICYCLO COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 12344268639     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048389m     Document Type: Article

References (29)

1. Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702.
2. See, for example: (a) Dömling, A. Comb. Chem. High Throughput Screening 1998, 1, 1-22. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169-3210. (c) Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647-658. (d) Ugi, I.; Heck, S Comb. Chem. High Throughput Screening 2001, 4, 1-34. (e) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (f) Ugi, I.; Werner, B.; Dömling, A. Molecules 2003, 8, 53-66 and references therein.
3. See, for example: (a) Dömling, A. Comb. Chem. High Throughput Screening 1998, 1, 1-22. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169-3210. (c) Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647-658. (d) Ugi, I.; Heck, S Comb. Chem. High Throughput Screening 2001, 4, 1-34. (e) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (f) Ugi, I.; Werner, B.; Dömling, A. Molecules 2003, 8, 53-66 and references therein.
4. See, for example: (a) Dömling, A. Comb. Chem. High Throughput Screening 1998, 1, 1-22. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169-3210. (c) Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647-658. (d) Ugi, I.; Heck, S Comb. Chem. High Throughput Screening 2001, 4, 1-34. (e) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (f) Ugi, I.; Werner, B.; Dömling, A. Molecules 2003, 8, 53-66 and references therein.
5. See, for example: (a) Dömling, A. Comb. Chem. High Throughput Screening 1998, 1, 1-22. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169-3210. (c) Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647-658. (d) Ugi, I.; Heck, S Comb. Chem. High Throughput Screening 2001, 4, 1-34. (e) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (f) Ugi, I.; Werner, B.; Dömling, A. Molecules 2003, 8, 53-66 and references therein.
6. See, for example: (a) Dömling, A. Comb. Chem. High Throughput Screening 1998, 1, 1-22. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169-3210. (c) Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647-658. (d) Ugi, I.; Heck, S Comb. Chem. High Throughput Screening 2001, 4, 1-34. (e) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (f) Ugi, I.; Werner, B.; Dömling, A. Molecules 2003, 8, 53-66 and references therein.
7. See, for example: (a) Dömling, A. Comb. Chem. High Throughput Screening 1998, 1, 1-22. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169-3210. (c) Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647-658. (d) Ugi, I.; Heck, S Comb. Chem. High Throughput Screening 2001, 4, 1-34. (e) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306-313. (f) Ugi, I.; Werner, B.; Dömling, A. Molecules 2003, 8, 53-66 and references therein.
8. See, for example: (a) Marquarding, D.; Hoffmann, P.; Heitzer, H.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 1969-1971. (b) Kunz, H.; Pfrengle, W.; Rück, K.; Sager, W. Synthesis 1991, 1039-1042. (c) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (d) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133.
9. See, for example: (a) Marquarding, D.; Hoffmann, P.; Heitzer, H.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 1969-1971. (b) Kunz, H.; Pfrengle, W.; Rück, K.; Sager, W. Synthesis 1991, 1039-1042. (c) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (d) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133.
10. See, for example: (a) Marquarding, D.; Hoffmann, P.; Heitzer, H.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 1969-1971. (b) Kunz, H.; Pfrengle, W.; Rück, K.; Sager, W. Synthesis 1991, 1039-1042. (c) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (d) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133.
11. See, for example: (a) Marquarding, D.; Hoffmann, P.; Heitzer, H.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 1969-1971. (b) Kunz, H.; Pfrengle, W.; Rück, K.; Sager, W. Synthesis 1991, 1039-1042. (c) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336-337. (d) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127-6133.
12. Demharter, A.; Horl, W.; Herdtweck, E.; Ugi, I. Angew. Chem., Int. Ed. 1996, 35, 173-175.
13. Sung, K.; Chen, F.-L.; Chung, M.-J. Mol. Div. 2003, 6, 213-221.
14. Basso, A.; Banfi, L.; Riva, R.; Guanti, G. Tetrahedron Lett. 2004, 45, 587-590.
15. 2 of the final amino acid derivative.
16. Bolm, C.; Schiffers, I.; Atodiresei, I.; Hackenberger, C. P. R. Tetrahedron: Asymmetry 2003, 14, 3455-3467.
17. 10 reported the Curtius rearrangement of the racemic azide of the bicyclic monomethyl ester in 84% yield; however, even after several attempts, we could not reproduce his results.
18. Canonne, P.; Akssira, M.; Dahdouh, A.; Kasmi, H.; Boumzebra, M. Tetrahedron 1993, 49, 1985-1992.
19. Sato, F.; Akiyama, T.; Iida, K.; Sato, M. Synthesis 1982, 1025-1026.
20. ElAmin, B.; Anantharamaiah, G. M.; Royer, G. P.; Means, G. E. J. Org. Chem. 1979, 44, 3442-3444.
21. 1H NMR in order to check the presence of a single diastereoisomer. In all cases the α-methoxy group could be univocally distinguished between the two diastereoisomers, as illustrated by the δ frequencies reported below. Mosher's amides: from 12a, (R) = 3.42, (S) = 3.33; from 12b, (R) = 3.39, (S) = 3.31; from 12c, (R) = 3.41, (S) = 3.33; from 12d, (R) = 3.53, (S) = 3.36; from 12e, (R) = 3.35, (S) = 3.51; from 12f, (R) = 3.28, (S) = 3.23; from 12g, (R) = 3.31, (S) = 3.39.
22. (a) Giordano, C.; Gallina, C.; Ottaviano, V.; Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1992, 27, 865-873.
23. (b) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schonholzer, P.; Spiegler, C.; Muller, K. Helv. Chim. Acta 1995, 78, 563-580.
24. (a) Ugi, I.; Kaufhold, G. Liebigs Ann. Chem. 1967, 709, 11-28.
25. (b) Ugi, I.; Offermann, K.; Herlinger, H.; Marquarding, D. Liebigs Ann. Chem. 1967, 709, 1-10.
26. (a) Flanagan, D. M.; Joullié, M. M. Synth. Commun. 1989, 19, 1-12.
27. (b) Bock, H.; Ugi, I. J. Prakt. Chem. 1997, 339, 385-389.
28. The four possible isomers of the postulated cyclic intermediate were minimized using MM2 (ChemBats3D software) and the energies compared, furnishing, as most stable isomer, the one reported in Figure 2.
29. 4 as the solvent, neither transient peaks nor any stable intermediate was observed by NMR, even after several days; however, after addition of the isocyanide, the reaction proceeded smoothly to give the desired Ugi adduct. A parallel experiment was conducted mixing compound 8 with benzyl isocyanide, but also in this case no transformation was observed until benzaldehyde was added to the mixture. These experiments do not prove but do not exclude the involvement of the postulated intermediate as metastable species in the reaction.