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Abstract | Cited by

The title reagent engaged in the modified Julia olefination with aldehydes under mild reaction conditions (DBU, CH2Cl2, rt or −78 °C) to yield α,β-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: Ethyl (benzothiazol-2-ylsulfonyl)acetate: a new reagent for the stereoselective synthesis of α,β-unsaturated esters from aldehydes

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