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Organic & Biomolecular Chemistry

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Org. Biomol. Chem., 2005, 3, 1365 - 1368, DOI: 10.1039/b500713e

Ethyl (benzothiazol-2-ylsulfonyl)acetate: a new reagent for the stereoselective synthesis of ,-unsaturated esters from aldehydes

Paul R. Blakemore, Danny K. H. Ho and W. Mieke Nap

The title reagent engaged in the modified Julia olefination with aldehydes under mild reaction conditions (DBU, CH2Cl2, rt or –78 °C) to yield ,-unsaturated esters; aryl aldehydes and aliphatic aldehydes possessing significant chain branching elements gave trans alkene products with high stereoselectivity (E : Z up to >98 : 2), while straight chain aliphatic aldehydes gave cis products preferentially (Z : E up to 92 : 8).

Graphical abstract image for this article (ID: b500713e)