Accession Number:

ADA232350

Title:

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

Descriptive Note:

Doctoral's thesis

Corporate Author:

AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OH

Personal Author(s):

Report Date:

1990-01-01

Pagination or Media Count:

283.0

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 THPTHF ring and the alpha-hydroxyester. The resolved compounds could be deprotonated and alkylated diastereoselectively with a variety of electrophiles. The diastereoselectivity ranged from 11 to 121 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.

Subject Categories:

  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE