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2005
Carboxylic acid esters
Q 0530
Ethyl(benzothiazol-2-ylsulfonyl)acetate: A New Reagent for the Stereoselective
Synthesis of α,β-Unsaturated Esters from Aldehydes. — Sulfone (III) is used for
37- 080 the
synthesis of α,β-unsaturated esters from aldehydes. Under mild conditions in the
presence of DBU, (E)-isomers are obtained as the major products. For the aliphatic aldehydes n-hexanal (IIIg) and citronellal (VII), (Z)-isomers are preferentially isolated.
When NaHMDS in refluxing THF is used, the (E)-isomer (Vg) can be isolated as the
main component. A complex mixture of intractable products is identified in the case of
cinnamaldehyde (IIIj). The reaction of phenylacetaldehyde (X) is non-regiospecific
and affords predominantly the β,γ-unsaturated ester (XII). — (BLAKEMORE*, P. R.;
HO, D. K. H.; NAP, W. M.; Org. Biomol. Chem. 3 (2005) 8, 1365-1368; Sch. Chem.,
Univ. Leeds, Leeds LS2 9JT, UK; Eng.) — S. Adam
2005
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