Amides typically prove to be poor nucleophiles, limiting their uses in the classic Aldol and Wittig reactions. Over the past 30 years few examples of the Weinreb amide's (a tertiary amide sporting a N-Electron Withdrawing Group) use in the Wittig reaction have appeared in the literature. Recent advances in the Wittig reaction, particularly the development of low temperature catalysis have spurred our interest in exploring its application to tertiary amides. Herein we report that catalytic Wittig conditions can be applied to tertiary amides affording trans-alkenes stereo-selectively. The need for an electron withdrawing group is demonstrated by comparison of the reactivity of the Weinreb amide with that of the morpholine and piperidine amides.
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