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) : Fryling, James A


Full Text : https://apps.dtic.mil/dtic/tr/fulltext/u2/a232350.pdf


Report Date : Jan 1990


Pagination or Media Count : 283


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.


Descriptors :   *SYNTHESIS , RESPONSE , ORGANIC MATERIALS , ACETALS , SEPARATION , ALKYLATION , COLUMN CHROMATOGRAPHY , PURITY , ETHERS


Subject Categories : Organic Chemistry


Distribution Statement : APPROVED FOR PUBLIC RELEASE