Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives

Org Lett. 2001 Nov 15;3(23):3753-5. doi: 10.1021/ol016708f.

Abstract

[reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to alpha,beta-unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives alpha-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to gamma-lactams, which can be easily converted into alpha-hydroxy-gamma-amino acid derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals*
  • Catalysis
  • Indicators and Reagents
  • Lithium Compounds*
  • Lithium*
  • Magnetic Resonance Spectroscopy
  • Silanes*

Substances

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