Enantiomerically Pure Acetals in Organic Synthesis: Resolutions and Diastereoselective Alkylations of Alpha-Hydroxy Esters
AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OH
Pagination or Media Count:
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.
- Organic Chemistry