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

Hao Li, Anyu He, John R. Falck, Lanny S. Liebeskind

Research output: Contribution to journalArticle

28 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)3682-3685
Number of pages4
JournalOrganic Letters
Volume13
Issue number14
DOIs
StatePublished - Jul 15 2011

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cross coupling
Ketones
Sulfhydryl Compounds
thiols
ketones
Copper
esters
Esters
copper
synthesis
thiophenes
carboxylates
amino acids
configurations
Amino Acids
alkoxyl radical

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Stereocontrolled synthesis of α-amino-α′-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes. / Li, Hao; He, Anyu; Falck, John R.; Liebeskind, Lanny S.

In: Organic Letters, Vol. 13, No. 14, 15.07.2011, p. 3682-3685.

Research output: Contribution to journalArticle

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