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Dynamic kinetic resolution of primary amines with a recyclable Pd nanocatalyst for racemization.

Organic letters (2007-02-13)
Mahn-Joo Kim, Won-Hee Kim, Kiwon Han, Yoon Kyung Choi, Jaiwook Park
RÉSUMÉ

A practical procedure for the dynamic kinetic resolution (DKR) of primary amines has been developed. This procedure employs a palladium nanocatalyst as the racemization catalyst, a commercial lipase (Novozym-435) as the resolution catalyst, and ethyl acetate or ethyl methoxyacetate as the acyl donor. Eleven primary amines and one amino acid amide have been efficiently resolved with good yields (85-99%) and high enantiomeric excesses (97-99%). [reaction: see text]

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Sigma-Aldrich
Palladium nanoparticle entrapped in aluminum hydroxide matrix, 0.5 wt. % loading