Debra J. Wallace

Cyclopropylboronic acid: synthesis and Suzuki cross-coupling reactions

An efficient synthesis of cyclopropylboronic acid is reported. This compound undergoes efficient Suzuki-type coupling reactions with a range of aryl and heteroarybromides.

Stereoselective double ring closing metathesis reactions in the synthesis of spirocyclic compounds

The first diastereoselective double ring closing metathesis reaction to afford a spirocyclic compound is reported. Cyclisation of amino acid derived tetraenes 7 selectively afforded spirocyclic compounds 8.

Copper-mediated reaction of 2-halopyridines with ethyl bromodifluoroacetate

Abstract A facile process for the preparation of substituted ethyl 2′-pyridyldifluoroacetates 3 is described starting from readily available ethyl bromodifluoroacetate 2 and substituted 2-bromo or 2-chloropyridines 1 . This process features a copper-mediated cross-coupling reaction in DMSO and is the first to utilise pyridylbromides or chlorides with ethyl bromodifluoroacetate 2 in this reaction.

Practical synthesis of a highly functionalized thiazole ketone

Abstract Compound 1 is a uniquely substituted ketone prepared via addition of a thiazole anion to an aromatic nitrile in good overall yield. An exploration into the generality of the addition of thiazole anions to nitriles allowed us to make a variety of thiazole ketones in good to excellent yields. The non-odorous thiolate-mediated demethylation reaction used in the synthesis of 1 is also presented.

A quadruple ring-closing metathesis reaction in the synthesis of bis-spirocyclic compounds: extending the scope of metathesis chemistry

The first example of a quadruple ring-closing metathesis reaction is reported. The reaction of the C2 symmetric octaene 3 afforded bis-spirocyclic compounds in high yield.

Ring-Closing Metathesis Reactions of Bis(enynes): Selectivity and Surprises

A study of the ring-closing metathesis reactions of two bis(enynes) is presented. These substrates, which contain two alkenes and two alkynes, as well as a resident stereocenter, can potentially generate metathesis products resulting from many reaction pathways. In this contribution we present our results on these reactions, show how small changes in reaction conditions can lead to different product ratios, and attempt to provide a rationale for the outcomes.