U-4C-3CR versus U-5C-4CR and stereochemical outcomes using suitable bicyclic β-amino acid derivatives as bifunctional components in the Ugi reaction

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 587-590

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

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

Chiral auxiliary; Intramolecular Ugi reaction; Multicomponent reactions; Stereoselective Ugi reaction; Ugi with secondary amines; Amino acids

Indexed keywords

AMINE; BETA AMINO ACID; CARBOXYL GROUP; CARBOXYLIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; SOLVENT EFFECT; STEREOCHEMISTRY; UGI REACTION;

EID: 0346993607     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.193     Document Type: Article

References (18)

1. Dömling A., Ugi I. Angew. Chem., Int. Ed. 39:2000;3169-3210.
2. Ugi I., Steinbruckner C. Chem. Ber. 94:1961;2802-2814 Isenring H.P., Hofheinz W. Synthesis. 1981;385-387 Obrecht R., Toure S., Ugi I. Heterocycles. 21:1984;271-277 Kehagia K., Ugi I. Tetrahedron. 51:1995;9523-9530 Dömling A., Kehagia K., Ugi I. Tetrahedron. 51:1995;9519-9522 Nitta H., Hatanaka M., Ishimura T. J. Chem. Soc., Chem. Commun. 1987;51-52.
3. Ugi I., Steinbruckner C. Chem. Ber. 94:1961;2802-2814 Isenring H.P., Hofheinz W. Synthesis. 1981;385-387 Obrecht R., Toure S., Ugi I. Heterocycles. 21:1984;271-277 Kehagia K., Ugi I. Tetrahedron. 51:1995;9523-9530 Dömling A., Kehagia K., Ugi I. Tetrahedron. 51:1995;9519-9522 Nitta H., Hatanaka M., Ishimura T. J. Chem. Soc., Chem. Commun. 1987;51-52.
4. Ugi I., Steinbruckner C. Chem. Ber. 94:1961;2802-2814 Isenring H.P., Hofheinz W. Synthesis. 1981;385-387 Obrecht R., Toure S., Ugi I. Heterocycles. 21:1984;271-277 Kehagia K., Ugi I. Tetrahedron. 51:1995;9523-9530 Dömling A., Kehagia K., Ugi I. Tetrahedron. 51:1995;9519-9522 Nitta H., Hatanaka M., Ishimura T. J. Chem. Soc., Chem. Commun. 1987;51-52.
5. Ugi I., Steinbruckner C. Chem. Ber. 94:1961;2802-2814 Isenring H.P., Hofheinz W. Synthesis. 1981;385-387 Obrecht R., Toure S., Ugi I. Heterocycles. 21:1984;271-277 Kehagia K., Ugi I. Tetrahedron. 51:1995;9523-9530 Dömling A., Kehagia K., Ugi I. Tetrahedron. 51:1995;9519-9522 Nitta H., Hatanaka M., Ishimura T. J. Chem. Soc., Chem. Commun. 1987;51-52.
6. Ugi I., Steinbruckner C. Chem. Ber. 94:1961;2802-2814 Isenring H.P., Hofheinz W. Synthesis. 1981;385-387 Obrecht R., Toure S., Ugi I. Heterocycles. 21:1984;271-277 Kehagia K., Ugi I. Tetrahedron. 51:1995;9523-9530 Dömling A., Kehagia K., Ugi I. Tetrahedron. 51:1995;9519-9522 Nitta H., Hatanaka M., Ishimura T. J. Chem. Soc., Chem. Commun. 1987;51-52.
7. Ugi I., Steinbruckner C. Chem. Ber. 94:1961;2802-2814 Isenring H.P., Hofheinz W. Synthesis. 1981;385-387 Obrecht R., Toure S., Ugi I. Heterocycles. 21:1984;271-277 Kehagia K., Ugi I. Tetrahedron. 51:1995;9523-9530 Dömling A., Kehagia K., Ugi I. Tetrahedron. 51:1995;9519-9522 Nitta H., Hatanaka M., Ishimura T. J. Chem. Soc., Chem. Commun. 1987;51-52.
8. Gokel G., Lüdke G., Ugi I. Ugi I. Isonitrile Chemistry. 1971;158 Academic, New York, Demharter A., Hörl W., Herdtweck E., Ugi I. Angew. Chem., Int. Ed. 35:1996;173-175 Ugi I., Demharter A., Hörl W., Schmid T. Tetrahedron. 52:1996;11657-11664 Zimmer R., Ziemer A., Gruner M., Brudgam I., Hartl H., Reissig H.U. Synthesis. 2001;1649-1658 Park S.J., Keum G., Kang S.B., Koh H.Y., Kim Y., Lee D.H. Tetrahedron Lett. 39:1998;7109-7112 Kim Y.B., Choi E.H., Keum G., Kang S.B., Lee D.H., Koh H.Y., Kim Y.S. Org. Lett. 3:2001;4149-4152.
9. Gokel G., Lüdke G., Ugi I. Ugi I. Isonitrile Chemistry. 1971;158 Academic, New York, Demharter A., Hörl W., Herdtweck E., Ugi I. Angew. Chem., Int. Ed. 35:1996;173-175 Ugi I., Demharter A., Hörl W., Schmid T. Tetrahedron. 52:1996;11657-11664 Zimmer R., Ziemer A., Gruner M., Brudgam I., Hartl H., Reissig H.U. Synthesis. 2001;1649-1658 Park S.J., Keum G., Kang S.B., Koh H.Y., Kim Y., Lee D.H. Tetrahedron Lett. 39:1998;7109-7112 Kim Y.B., Choi E.H., Keum G., Kang S.B., Lee D.H., Koh H.Y., Kim Y.S. Org. Lett. 3:2001;4149-4152.
10. Gokel G., Lüdke G., Ugi I. Ugi I. Isonitrile Chemistry. 1971;158 Academic, New York, Demharter A., Hörl W., Herdtweck E., Ugi I. Angew. Chem., Int. Ed. 35:1996;173-175 Ugi I., Demharter A., Hörl W., Schmid T. Tetrahedron. 52:1996;11657-11664 Zimmer R., Ziemer A., Gruner M., Brudgam I., Hartl H., Reissig H.U. Synthesis. 2001;1649-1658 Park S.J., Keum G., Kang S.B., Koh H.Y., Kim Y., Lee D.H. Tetrahedron Lett. 39:1998;7109-7112 Kim Y.B., Choi E.H., Keum G., Kang S.B., Lee D.H., Koh H.Y., Kim Y.S. Org. Lett. 3:2001;4149-4152.
11. Gokel G., Lüdke G., Ugi I. Ugi I. Isonitrile Chemistry. 1971;158 Academic, New York, Demharter A., Hörl W., Herdtweck E., Ugi I. Angew. Chem., Int. Ed. 35:1996;173-175 Ugi I., Demharter A., Hörl W., Schmid T. Tetrahedron. 52:1996;11657-11664 Zimmer R., Ziemer A., Gruner M., Brudgam I., Hartl H., Reissig H.U. Synthesis. 2001;1649-1658 Park S.J., Keum G., Kang S.B., Koh H.Y., Kim Y., Lee D.H. Tetrahedron Lett. 39:1998;7109-7112 Kim Y.B., Choi E.H., Keum G., Kang S.B., Lee D.H., Koh H.Y., Kim Y.S. Org. Lett. 3:2001;4149-4152.
12. Gokel G., Lüdke G., Ugi I. Ugi I. Isonitrile Chemistry. 1971;158 Academic, New York, Demharter A., Hörl W., Herdtweck E., Ugi I. Angew. Chem., Int. Ed. 35:1996;173-175 Ugi I., Demharter A., Hörl W., Schmid T. Tetrahedron. 52:1996;11657-11664 Zimmer R., Ziemer A., Gruner M., Brudgam I., Hartl H., Reissig H.U. Synthesis. 2001;1649-1658 Park S.J., Keum G., Kang S.B., Koh H.Y., Kim Y., Lee D.H. Tetrahedron Lett. 39:1998;7109-7112 Kim Y.B., Choi E.H., Keum G., Kang S.B., Lee D.H., Koh H.Y., Kim Y.S. Org. Lett. 3:2001;4149-4152.
13. Gokel G., Lüdke G., Ugi I. Ugi I. Isonitrile Chemistry. 1971;158 Academic, New York, Demharter A., Hörl W., Herdtweck E., Ugi I. Angew. Chem., Int. Ed. 35:1996;173-175 Ugi I., Demharter A., Hörl W., Schmid T. Tetrahedron. 52:1996;11657-11664 Zimmer R., Ziemer A., Gruner M., Brudgam I., Hartl H., Reissig H.U. Synthesis. 2001;1649-1658 Park S.J., Keum G., Kang S.B., Koh H.Y., Kim Y., Lee D.H. Tetrahedron Lett. 39:1998;7109-7112 Kim Y.B., Choi E.H., Keum G., Kang S.B., Lee D.H., Koh H.Y., Kim Y.S. Org. Lett. 3:2001;4149-4152.
14. Gedey S., Van der Eycken J., Fulöp F. Org. Lett. 4:2002;1967-1969.
15. To confirm unambiguously the absence of the second diastereoisomer, the two diastereoisomers of compound 6f were independently prepared via an alternative procedure and their NMR spectra were compared with the one of the crude material of the Ugi reaction of compound 1b with isobutyric aldehyde and benzyl isocyanide, confirming that only one diastereoisomer could be detected within the limits of the NMR sensitivity.
16. 9 of exo-3,6-epoxy-1,2,3,6-tetrahydro-phthalic acids prior to the Curtius rearrangement generating the amino acid moiety.
17. Guanti G., Banfi L., Narisano E., Riva R., Thea S. Tetrahedron Lett. 27:1986;4639-4642.
18. Chen Y., McDaid P., Deng L. Chem. Rev. 103:2003;2965-2983.