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

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

*School of Chemistry, University of Leeds, Leeds, UK LS2 9JT, Email: paul.blakemorescience.oregonstate.edu

P. R. Blakemore, D. K. H. Ho, W. M. Nap, Org. Biomol. Chem., 2005, 3, 1365-1368.

DOI: 10.39/b500713e


Abstract

Ethyl (benzothiazol-2-ylsulfonyl)acetate engaged in the modified Julia olefination with aldehydes under mild reaction conditions to yield α,β-unsaturated esters. Aryl aldehydes and aliphatic aldehydes possessing significant chain branching elements gave trans alkene products with high stereoselectivity, while straight chain aliphatic aldehydes gave cis products preferentially.

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Key Words

Modified Julia Olefination, α,β-unsaturated esters


ID: J52-Y2005-480