Abstract

AbstractThe pairing of unstabilized nitrogen ylides generated in situ with functionalized thiolesters under ambient conditions resulted in a new intramolecular carbon–carbon bond forming reaction. The scope of the reaction was illustrated with a series of substituted thiolester substrates. This reaction represents a new method for the synthesis of 2‐substituted tetrahydrothienyl compounds through a unique 1,2‐thiolate shift. Whereas nitrogen ylides have been used in synthesis previously, very few examples exist in which unstabilized nitrogen ylides have been utilized in synthetically meaningful transformations.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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