- Anti-configured protected α,β-diamino acids are prepared with up to 99% ee using a direct catalytic enantioselective Mannich reaction. A catalyst system incorporating a chiral bis(oxazoline) ligand, Mg(ClO4)2 and Hünigs base, promotes the addition of an isothiocyanate-substituted imide to a variety of aryl-, heteroaryl-, alkenyl-, and alkyl-derived imines. Conversion of the products to their iPr-ester derivatives allows epimerization to the syn-diastereomers. Copyright © 2007 American Chemical Society.
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Direct catalytic enantioselective Mannich reactions: synthesis of protected anti-alpha,beta-diamino acids.
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