81503-25-5Relevant academic research and scientific papers
Behaviour of dioxolanones as chiral acyl anion equivalents
Aitken, R. Alan,Thomas, Andrew W.
, p. 102 - 104 (2007/10/03)
The 1,3-dioxolan-4-ones readily derived from α-hydroxy acids act as convenient acyl anion equivalents by deprotonation - alkylation followed by flash vacuum pyrolysis. Conjugate addition of their anions to ethyl crotonate similarly gives β-methyl-γ-oxo esters and by using chiral dioxolanones these can be obtained in up to 86% e.e.
Synthesis and lipase-catalyzed resolution of 5-(hydroxymethyl)-1,3-dioxolan-4-ones: Masked glycerol analogs as potential building blocks for pharmaceuticals
Hof, Robert P.,Kellogg, Richard M.
, p. 3423 - 3427 (2007/10/03)
(Hydroxymethyl)-1,3-dioxolan-4-ones from mandelic and lactic acids and 1,5,5-trimethyl-3-phenyloxazolidin-2-one from mandelamide were α-alkylated using benzyl chloromethyl ether. Reductive debenzylation of the products of alkylation unmasked the hydroxymethyl groups. The compounds obtained in this fashion were subsequently subjected to lipase-catalyzed resolution in organic media. Depending on the lipase and substrate employed, enantiomeric ratios up to E = 200 were observed. The obtained optically pure compounds can be considered as masked 2-substituted glycerol equivalents, which could be used for the preparation of tertiary (aryloxy)propanolamines, compounds having potential β-blocking activity.
