Nucleophilic substitution at the acetalic center of mandelate 1,3-dioxolan-4-ones using magnesio-copper reagents: Application to the synthesis of chiral secondary alcohols.

Bertrand Heckmann, Charles Mioskowski, Jurong Yu, J R Falck

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Ethereal magnesio-copper reagents, in contrast to lithio-copper reagents, add stereoselectively to mandelic acid derived 1,3-dioxolan-4-ones to afford optically active secondary alcohols after removal of the chiral auxiliary.

Original languageEnglish (US)
Pages (from-to)5201-5204
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number36
DOIs
StatePublished - Sep 1 1992

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Copper
Substitution reactions
Alcohols
mandelic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Nucleophilic substitution at the acetalic center of mandelate 1,3-dioxolan-4-ones using magnesio-copper reagents : Application to the synthesis of chiral secondary alcohols. / Heckmann, Bertrand; Mioskowski, Charles; Yu, Jurong; Falck, J R.

In: Tetrahedron Letters, Vol. 33, No. 36, 01.09.1992, p. 5201-5204.

Research output: Contribution to journalArticle

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abstract = "Ethereal magnesio-copper reagents, in contrast to lithio-copper reagents, add stereoselectively to mandelic acid derived 1,3-dioxolan-4-ones to afford optically active secondary alcohols after removal of the chiral auxiliary.",
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