Absolute structure determination of (2R,1′S)-2-(1′-benzyl-2′-hydroxyethylamino)-4-phenylbutanoic acid

Add time:08/21/2019    Source:sciencedirect.com

Crystallization-induced asymmetric transformation was employed to prepare a labile γ-oxo-α-aminoacid (3) with a new stereogenic center in high diastereomeric and enantiomeric purity. Compound 3 was reduced to a stable compound, (2R,1′S)-2-(1′-benzyl-2′-hydroxyethylamino)-4-phenylbutanoic acid (4), which crystallizes in space group P21. Upon deprotonation, 4 becomes a tridentate monoanionic chelating ligand, 4−H, which reacts with copper nitrate yielding [Cu(4−H)(H2O)2]NO3·H2O (5). Complex 5 crystallizes in space group P21 and has a rare composition among crystallographically characterized mononuclear five-coordinate transition metal complexes. The absolute structure determination of 5 allowed by inference the assignment of absolute configuration to compound 3.

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