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  • Title: Ethyl (benzothiazol-2-ylsulfonyl)acetate: a new reagent for the stereoselective synthesis of alpha,beta-unsaturated esters from aldehydes.
    Author: Blakemore PR, Ho DK, Nap WM.
    Journal: Org Biomol Chem; 2005 Apr 21; 3(8):1365-8. PubMed ID: 15827628.
    Abstract:
    The title reagent engaged in the modified Julia olefination with aldehydes under mild reaction conditions (DBU, CH(2)Cl(2), rt or -78 degrees C) to yield alpha,beta-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).
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