Amino acid-catalyzed dynamic kinetic asymmetric transformations (DYKAT): one-step de novo synthesis of polyketide sugars from racemic beta-hydroxy aldehydes

摘要

The ability of amino acids to catalyze dynamic kinetic asymmetric transformation (DYKAT) with excellent stereoselectivity is presented. The novel DYKAT process was applied in the proline-catalyzed one-step de novo synthesis of triketide- and deoxysugars, which were formed with excellent diastereoselectivity and up to 99% ee. The de novo synthesis is accomplished via an enzyme-like DYKAT process, which includes continuous amino acid-mediated racemization of the acceptor beta-hydroxy aldehyde in combination with amino acid-catalyzed direct selective aldol addition. (c) 2005 Elsevier Ltd. All rights reserved.