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Chemoenzymatic synthesis and properties of Schiff bases containing (R)-1-(9-anthryl)ethylamine

✍ Scribed by Marin Roje; Vitomir Šunjić

Book ID
102072794
Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
113 KB
Volume
14
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

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.

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