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Organic letters

Stereocontrolled synthesis of α-amino-α'-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes.


PMID 21675755

Abstract

A stereocontrolled synthesis of α-amino-α'-alkoxy ketones is described. This pH-neutral copper(I) thiophene-2-carboxylate (CuTC)-catalyzed cross-coupling of amino acid thiol esters and chiral nonracemic α-alkoxyalkylstannanes gives α-amino-α'-alkoxy ketones in good to excellent yields with complete retention of configuration at the α-amino- and α-alkoxy-substituted stereocenters.

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