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Addition of Silyl Ketene Acetals to Nitrones Catalyzed by Lanthanide Triflates

Authors :
Changtao Qian
Longcheng Wang
Source :
Tetrahedron. 56:7193-7197
Publication Year :
2000
Publisher :
Elsevier BV, 2000.

Abstract

α-Aryl-N-phenyl nitrones reacted with silyl ketene acetals mediated by lanthanum trifloromethanesulfonate (triflate) to afford the addition product in excellent yield under mild conditions. α-Aryl-N-tert-butyl nitrone reacted with ethyl trimethylsilylacetate to yield the unexpected α,β-unsaturated ester in a 100% E-form. A possible mechanism for the process is discussed.

Details

ISSN :
00404020
Volume :
56
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........a37905c6e7e6883e2a2541a4d01c61cd
Full Text :
https://doi.org/10.1016/s0040-4020(00)00636-0