Ethyl (benzothiazol-2-ylsulfonyl)acetate: a new reagent for the stereoselective synthesis of alpha,beta-unsaturated esters from aldehydes |
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| Authors: | Blakemore Paul R Ho Danny K H Nap W Mieke |
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| Affiliation: | School of Chemistry, University of Leeds, West Yorkshire, UK. paul.blakemore@science.oregonstate.edu |
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| 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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