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Lewis acid promoted diastereoselective Mannich reaction of beta-lactam - tethered aldimines with 1-methoxy-1-trimethylsilyloxy-2, 2-dimethylethene


Vazdar, Katarina; Margetić, Davor; Habuš, Ivan
Lewis acid promoted diastereoselective Mannich reaction of beta-lactam - tethered aldimines with 1-methoxy-1-trimethylsilyloxy-2, 2-dimethylethene // Heterocycles, 83 (2011), 1; 63-90 doi:10.3987/COM-10-12097 (međunarodna recenzija, članak, znanstveni)


Naslov
Lewis acid promoted diastereoselective Mannich reaction of beta-lactam - tethered aldimines with 1-methoxy-1-trimethylsilyloxy-2, 2-dimethylethene

Autori
Vazdar, Katarina ; Margetić, Davor ; Habuš, Ivan

Izvornik
Heterocycles (0385-5414) 83 (2011), 1; 63-90

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

Ključne riječi
Beta-Lactam; Diastereoselective Mannich reaction; beta-Amino acid ester; Lewis acid

Sažetak
Lewis acid (ZnI2) – promoted Mannich reaction of azetidin-2-one – tethered aldimines 3a-r with silylenol ether 4 in toluene at –20 °C afforded a diastereomeric mixture of beta-amino acid esters 5a-r/6a-r. The effect of the amount of zinc(II) iodide, equimolar (100 mol%) and catalytic (20 mol%), on the chemical yield and the product stereoisomeric ratio was studied. The diastereoselective Mannich reaction of imine 3a with silylenol ether 4 at low temperature (–20 °C) in toluene under equimolar zinc(II) iodide catalysis provided the best chemical yield – 99% combined with the highest diastereoselectivity of beta-amino acid esters 5a/6a – 85:15%. Furthermore, the influence of various groups on azetidin-2-one – tethered imines 3a-r (R1 = phenyl, ferrocenyl ; R2 = alkyl, aryl, ferrocenyl) has been applied in the Mannich reaction leading to the formation of two stereoisomers of beta-amino acid esters 5a-r/6a-r with diastereomeric ratio varying from 92:8 to 59:41%.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982915-2948 - Amino-beta-laktami - intermedijari u sintezi biološki interesantnih spojeva (Vlasta Tomašić, )
098-0982933-3218 - 'Host-guest' međudjelovanja u policikličkim sustavima (Davor Margetić, )

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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