Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters

Jessica A. Griswold, Matthew A. Horwitz, Leslie V. Leiva, Jeffrey S. Johnson

Research output: Research - peer-reviewArticle

  • 2 Citations

Abstract

A quinidine-catalyzed diastereoselective addition of α-angelica lactone to β-halo-α-ketoesters is reported. The α-angelica lactone displays unusual regioselectivity in this reaction, acting as a nucleophile at the α-position to provide fully substituted glycolic esters with three contiguous stereocenters. Subsequent diastereoselective hydrogenation provides an additional stereocenter within the lactone.

LanguageEnglish (US)
Pages2276-2280
Number of pages5
JournalJournal of Organic Chemistry
Volume82
Issue number4
DOIs
StatePublished - Feb 17 2017

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angelica lactone
Regioselectivity
Nucleophiles
Quinidine
Lactones
Hydrogenation
Esters

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters. / Griswold, Jessica A.; Horwitz, Matthew A.; Leiva, Leslie V.; Johnson, Jeffrey S.

In: Journal of Organic Chemistry, Vol. 82, No. 4, 17.02.2017, p. 2276-2280.

Research output: Research - peer-reviewArticle

Griswold, Jessica A. ; Horwitz, Matthew A. ; Leiva, Leslie V. ; Johnson, Jeffrey S./ Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 4. pp. 2276-2280
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