Enantioselective synthesis of α-hydroxy carboxylic acids

Direct conversion of α-oxocarboxylic acids to enantiomerically enriched α-hydroxy carboxylic acids via neighboring group control

Zhe Wang, Brittany La, Joseph M. Fortunak, Xian Jun Meng, George Kabalka

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

α-Oxocarboxylic acids can be reduced to the corresponding α-hydroxy carboxylic acids employing DIP-CI(TM) as a reducing agent. The α-carboxylic substituent exerts a remarkable neighboring group effect on the reduction. The reaction presumably proceeds in an intramolecular fashion through a 'rigid' bicyclic transition state assembly, which produces enantioselectivities approaching 99%.

Original languageEnglish (US)
Pages (from-to)5501-5504
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number31
DOIs
StatePublished - Jul 30 1998

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Hydroxy Acids
Enantioselectivity
Reducing Agents
Carboxylic Acids
Control Groups
Acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Enantioselective synthesis of α-hydroxy carboxylic acids : Direct conversion of α-oxocarboxylic acids to enantiomerically enriched α-hydroxy carboxylic acids via neighboring group control. / Wang, Zhe; La, Brittany; Fortunak, Joseph M.; Meng, Xian Jun; Kabalka, George.

In: Tetrahedron Letters, Vol. 39, No. 31, 30.07.1998, p. 5501-5504.

Research output: Contribution to journalArticle

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