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Synthesis and structure determination of methyl (3S)- and (3R)-(trans-(3'R, 4'R)-3-amino-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl)-2, 2-dimethyl-3-ferrocenylpropanoate


Radolović, Katarina; Molčanov, Krešimir; Habuš, Ivan
Synthesis and structure determination of methyl (3S)- and (3R)-(trans-(3'R, 4'R)-3-amino-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl)-2, 2-dimethyl-3-ferrocenylpropanoate // Journal of molecular structure, 966 (2010), 1-3; 8-13 doi:10.1016/j.molstruc.2009.11.056 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis and structure determination of methyl (3S)- and (3R)-(trans-(3'R, 4'R)-3-amino-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl)-2, 2-dimethyl-3-ferrocenylpropanoate

Autori
Radolović, Katarina ; Molčanov, Krešimir ; Habuš, Ivan

Izvornik
Journal of molecular structure (0022-2860) 966 (2010), 1-3; 8-13

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Asymmetric Mannich reaction ; beta-Lactam ; Ferrocene ; Imine ; Lewis acid ; X-Ray structure

Sažetak
Lewis acid (ZnI2) - promoted Mannich reaction of azetidin-2-one - tethered aldimine 3 with silylenol ether 4 in toluene at - 20 oC afforded a diastereomeric mixture of beta-amino acid esters 5 and 6 in ratio 65:35. Diastereomers 5 and 6 were chromatographycally separated and their crystal structure determined in order to establish unambigously both absolute and relative configurations at the stereogenic centers C11, C12, and C14. The final value of the freely refined Flack parameter of diastereomer 6, x = -0.003 (3), unambigously indicates that all three centers have the R configuration. According to the synthetic procedure, configurations on C12 and C14 of diastereomer 5 have the same R orientation as of diastereomer 6, therefore Friedel pairs for the structure of 5 were not measured. Furthermore, S configuration on C11 of diastereomer 5 was assigned in relation to R configuration at C12 and C14 stereogenic centers.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982915-2948 - Amino-beta-laktami - intermedijari u sintezi biološki interesantnih spojeva (Vlasta Tomašić, )
098-1191344-2943 - Protein-ligand međudjelovanja na atomnoj razini (Marija Luić, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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