Diastereoselective method of preparing olefins by means of the horner-wadsworthemmons reaction, comprising the addition of a tris-(polyoxaalkyl)-amine sequestering agent
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United States of America Patent
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Issued Date -
May 11, 2006
app pub date -
Sep 22, 2003
filing date -
Sep 23, 2002
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Abandoned
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Abstract
The invention relates to a process for the diastereoselective preparation of olefins via the Homer-Wadsworth-Emmons reaction, which consists in reacting at low temperature a phosphonate with a carbonyl derivative in the presence of a base in a suitable solvent, characterized in that a tris(polyoxaalkyl)amine sequestering reagent of formula (I): N--[CHR.sub.1--CHR.sub.2--O--(CHR.sub.3--CHR.sub.4--O).sub.n--R.sub.5].su-b.3 (I), wherein: n is an integer between 0 and 10; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be identical or different, and represent a hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms; R.sub.5 represents a hydrogen atom, an alkyl or cycloalkyl radical containing up to 12 carbon atoms, a phenyl radical or a radical of formula --C.mu.H2.mu.-.PHI., or C.sub.mH.sub.2m+1-.PHI.-, with m being an integer between 1 and 12 and .PHI. being a phenyl radical; is added in an amount that is sufficient to increase the diastereoselectivity of the olefin.
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