Enantiomerically Pure Acetals in Organic Synthesis: Resolutions and Diastereoselective Alkylations of Alpha-Hydroxy Esters

Abstract

The diastereomeric tetrahydropyranyl (THP) and tetrahydrofuranyl (THF) ethers of a variety of alpha-hydroxyestes were synthesized and separated by column chromatography. The separability of the diastereomers was found to be a general phenomenon which allowed for wide variations in both the THP/THF ring and the alpha-hydroxyester. The resolved compounds could be deprotonated and alkylated diastereoselectively with a variety of electrophiles. The diastereoselectivity ranged from 1:1 to 12:1 depending on the alpha- hydroxyester, the alkylating agent, and the reaction conditions. In most cases the diastereomeric products of the alkylation were also separated by column chromatography.

Open PDF

Document Details

Document Type
Technical Report
Publication Date
Jan 01, 1990
Accession Number
ADA232350

Entities

People

  • James A. Fryling

Organizations

  • Air Force Institute of Technology

Tags

Communities of Interest

  • C4I

DTIC Thesaurus Topics

  • Alcohols
  • Alkenes
  • Biological Products
  • Chemical Reactants
  • Chemical Shifts
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Column Chromatography
  • Crystal Structure
  • Ketones
  • Materials
  • Organic Chemistry

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry