Naslov
Chemoenzymatic Synthesis and Properties of Schiff Bases Containing (R)-1-(9-Anthryl)ethylamine

Autori
Roje, Marin ; Šunjić, Vitomir

Izvornik
Chirality (0899-0042) 14 (2002); 625-631

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

Ključne riječi
Kinetic resolution; Lipase catalyzed acetylation; Catalytic cyclopropanation; Circular dichroism (cd)

Sažetak
Racemic 1-(9-anthryl)ethylamine (10), obtained in 70% overall yield from commercial 9-cyanoanthracene, was kinetically resolved by the Candida antarctica A lipase-catalyzed acetylation with isopropyl acetate as acyl donor, affording (R)-(+)-10 with 95.8% enantiomeric excess (e.e.) (E-value 43.5), which afforded Schiff bases (R)-4 and(R)-8. H-1-NMR, CD, and MM2 calculations offer a consistent picture of the conformational properties of these potential ligands and an explanation for the limited enhancement of enantioselectivity in cyclopropanation of styrene by their Cu(I) complexes, as compared with previously studied ligands in this series.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA