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Chemoenzymatic synthesis and properties of Schiff bases containing ( R )‐1‐(9‐anthryl)ethylamine
Author(s) -
Roje Marin,
Šunjić Vitomir
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10126
Subject(s) - ethylamine , chemistry , isopropyl , chirality (physics) , enantiomeric excess , cyclopropanation , enantiomer , candida antarctica , yield (engineering) , stereochemistry , medicinal chemistry , acetylation , lipase , organic chemistry , catalysis , enantioselective synthesis , enzyme , chiral symmetry breaking , physics , materials science , quantum mechanics , nambu–jona lasinio model , metallurgy , quark , biochemistry , gene
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. 1 H‐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. Chirality 14:625–631, 2002. © 2002 Wiley‐Liss, Inc.