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

Authors
Dussault, PH Lee, RJ Schultz, JA Suh, YS
Citation
Ph. Dussault et al., Reaction of peroxyacetals with silyl ketene acetals: synthesis of 3-peroxyalkanoates and 3-peroxyalkanals, TETRAHEDR L, 41(29), 2000, pp. 5457-5460
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
29
Year of publication
2000
Pages
5457 - 5460
Database
ISI
SICI code
0040-4039(20000715)41:29<5457:ROPWSK>2.0.ZU;2-6
Abstract
Lewis acid-mediated reaction of monoperoxyacetals with silyl ketene acetals (SKAs) provides an efficient approach to 3-peroxyalkanoates. Propionate SK As react with aliphatic peroxyacetals to furnish 3-peroxy-2-methyl alkanoat es with modest anti-selectivity. Although acetate and thioacetate SKAs are less reactive, the latter react with unsaturated peroxyacetals to furnish p eroxyalkenoates and -alkadienoates which undergo chemoselective reduction t o 3-peroxyalkenals and 3-peroxyalkadienals. (C) 2000 Elsevier Science Ltd. All rights reserved.