Fundação para a Ciência e a Tecnologia (FCT) - PTDC/QUI/67407/200

Alves, M. José

Duarte, Vera C. M.

Fortes, A. Gil

Salgueiro, D. A. L.

Sousa, C. E. A.

Universidade do Minho: RepositoriUM

The Synthesis of an Homochiral Aziridine as a Useful Synton to Iminosugars and Amino Acid Compounds  Sousa, C.E.A., Alves, M.J., Gil Fortes, A., Salgueiro, D.A.L., Duarte, Vera C.M. University of Minho, Chemistry Research Centre, Campus de Gualtar, 4710-057 Braga, PT. criz.sousa@hotmail.com  The starting aldehyde 1 is described in lit., obtained from D-glucose.[1] It suffer elongation by a Wittig reaction giving 2.3:1 ratio of the cis and trans isomers 2 respectively. The mixture was solubilized in toluene, and silica was added. The mixture was heated in the rotary evaporator until the cis isomer disappeared. The desired δ-lactam 3 was obtained. The α,β-unsaturated system of the lactam was looked as an electron-withdrawing dipolarophile, combined with the electron rich benzylazide, as dienophile and heated under an acid scavenger (trimetylortoformate). A totally selective reaction occurred giving compound 4 in 88% yield. Photolysis of the compound 4 gave the final aziridine 5 after 1h 50 min in MeOH. Finally the lactam was opened again with sodium methoxide giving 6. The NMR of the crucial compounds will be presented together with an X-ray of compound 4. O OOHPhCO2MeO OOHPhO +O OOHPhMeO2C 2.3 : 1O OOPhOBnN3CH(OMe)3, ref.O OOPhONNNBn O OOPhON Bn254 nmMeOH1.50h70 ºCToluene,     SiO2NaOMe/HOMe O OPhON BnMeOOHPh3CHCO2MeTHF secoScheme 11 23 4 5 6  Acknowledgements : We thanks to FCT (Project PTDC/QUI/67407/2006), QREN, COMPETE and POPH for financial support and to the Portuguese NMR Network  RNRMN (Bruker Avance II 400).  References: [1] Baker, S.R.; Clissold, D.W.; McKillop, A. Tetrahedron Lett. 1988, 29, 991-994; Zimmermann, P.; Schmidt, R.R. Liebigs Annal. Chem. 1988, 663-667. 

The synthesis of an homochiral aziridine as a useful synton to iminosugars and amino acid compounds

http://repositorium.sdum.uminho.pt/bitstream/1822/15123/1/abstract-Cristina.pdf

The synthesis of an homochiral aziridine as a useful synton to iminosugars and amino acid compounds

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Universidade do Minho: RepositoriUM