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2005
Olefination
O 0284
12- 061
Sequential Olefinations on 2-Arylmethylidene-2-phosphonoacetates: A One-Pot
Highly Stereoselective Synthesis of 1,2,3-Trisubstituted 1,3-Butadienes. — Arylmethylidenephosphonoacetates (III) are synthesized by a Knoevenagel-type reaction
and subjected to reaction with a combination of trimethylsulfonium iodide (IV) and sodium dimsylate, which acts as a carbene equivalent. The reaction is quenched by aldehydes (V) to complete this one-pot sequential double olefination for the synthesis of
substituted 1,3-dienes (VI). Although the yields are moderate, the products are obtained
exclusively as (Z)-isomers and are easily isolable by chromatography because the
by-products are highly polar or water soluble. — (DATE, S. M.; GHOSH*, S. K.;
Bull. Chem. Soc. Jpn. 77 (2004) 11, 2099-2100; Bio-Org. Div., Bhabha At. Res. Cent.,
Trombay, Bombay 400 085, India; Eng.) — H. Hoennerscheid
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