Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters

Org Lett. 2001 Nov 15;3(23):3749-52. doi: 10.1021/ol016707n.

Abstract

[reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals*
  • Alkylation
  • Catalysis
  • Esters
  • Indicators and Reagents
  • Lithium Compounds*
  • Lithium*
  • Silanes*
  • Stereoisomerism

Substances

  • Acetals
  • Esters
  • Indicators and Reagents
  • Lithium Compounds
  • Silanes
  • butane-2,3-diacetal glycolic acid
  • Lithium
  • lithium hexamethyldisilazide