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Reaction of peroxyacetals with silyl ketene acetals: synthesis of 3-peroxyalkanoates and 3-peroxyalkanals

✍ Scribed by P.H Dussault; R.J Lee; J.A Schultz; Y.S Suh

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
163 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

Lewis acid-mediated reaction of monoperoxyacetals with silyl ketene acetals (SKAs) provides an ecient approach to 3-peroxyalkanoates. Propionate SKAs react with aliphatic peroxyacetals to furnish 3-peroxy-2-methyl alkanoates with modest anti-selectivity. Although acetate and thioacetate SKAs are less reactive, the latter react with unsaturated peroxyacetals to furnish peroxyalkenoates and -alkadienoates which undergo chemoselective reduction to 3-peroxyalkenals and 3-peroxyalkadienals.

πŸ“œ SIMILAR VOLUMES

Reaction of nitrones with silyl ketene a
Reaction of nitrones with silyl ketene acetals: A DFT study
✍ Anne Milet; Yves Gimbert; Andrew E. Greene πŸ“‚ Article πŸ“… 2006 πŸ› John Wiley and Sons 🌐 English βš– 389 KB

## Abstract Theoretical calculations at the DFT level indicate that the reaction of a nitrone with a silyl ketene acetal proceeds, contrary to previous suggestions, through a classical 1,3‐dipolar cycloaddition, followed by a silyl group transfer step to give the open‐chain product. Introduction of