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

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

SUBMITTER: Li H

PROVIDER: S-EPMC3499733 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature

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

Li Hao H He Anyu A Falck John R JR Liebeskind Lanny S LS

Organic letters 20110615 14

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. ...[more]

PMID: 21675755

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