10.1021/ol802745n.s001
M. Daniel Spantulescu
M. Daniel
Spantulescu
Marc A. Boudreau
Marc A.
Boudreau
John C. Vederas
John C.
Vederas
Retention of Configuration in Photolytic Decarboxylation of Peresters to Form Chiral Acetals and Ethers
American Chemical Society
2009
malic acids
site
decarboxylation
ether
retention
Chiral acyclic acetals
absence
wavelength UV light
Configuration
tartaric
Photolytic Decarboxylation
stereochemical control
temperature results
configuration
carbonyl
photolyzed
Ethers Peresters
precursor
yield
process proceeds
Form Chiral Acetals
2009-02-05 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Retention_of_Configuration_in_Photolytic_Decarboxylation_of_Peresters_to_Form_Chiral_Acetals_and_Ethers/2880871
Peresters generate ethers in good yields when photolyzed in the absence of solvent using short wavelength UV light. At −78 °C or below, the process proceeds predominantly with retention of configuration at the site adjacent to the carbonyl where the decarboxylation occurs, but increase in temperature results in loss of stereochemical control. Chiral acyclic acetals can be prepared using precursors derived from tartaric or malic acids.