Eduardo Sánchez-Larios

• PhD, Organic Chemistry
• University of Saskatchewan

Schreiber's gold(I)-catalyzed synthesis of α-pyrones was adapted to the total synthesis of a ring A aromatic podolactone, urbalactone. The scope of the acetylenic ester partner in the formation of α-pyrones was studied. The total synthesis features, as key steps, α-pyrone formation, Friedel–Crafts cyclization, Stille coupling, and a N,N′-dicyclohex...

A practical and chromatography-free synthesis of vinamidinium salts and their use as diene precursors in Diels-Alder reactions is reported. Additionally, 1,3-dipyrrolidino-1,3-butadiene was shown to be significantly more reactive than Rawal's diene in a competition experiment.

Various NHC-catalyzed domino transformations involving dimerization of o-formylchalcone substrates or their combination with dialdehyde derivatives (IV) are investigated.

The use of β,γ-unsaturated-α-ketoesters in the intermolecular Stetter reaction furnishes 1,2,5-tricarbonyl compounds in high yield and excellent enantioselectivity. The α,δ-diketoesters generated using this methodology serve as useful synthetic building blocks via chemo- and diastereoselective transformations.

The synthesis of spiro bis-indanes by means of N-heterocyclic carbene (NHC) catalysis is reported. The dimerization of various o-formyl chalcone substrates or their combination with phthaldialdehyde derivatives under the catalysis of thiazolium-derived carbenes afforded Stetter-aldol-Michael products and Stetter-aldol-aldol products, respectively....

Two novel domino NHC-catalyzed spirocyclizations are described herein, enabling the rapid construction of three new carbon-carbon bonds and a quaternary center with high diastereoselectivity. A variety of spiro bis-indane structures are assembled in a single step from simple o-phthaldialdehyde derivatives.

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N-Heterocyclic carbenes were found to catalyze a domino Stetter-Michael reaction for the synthesis of indanes. The products were obtained in good yield and diastereomeric ratio, allowing access to highly functionalized indanes under mild conditions. In addition, the functional groups present on the indanes could be used for the synthesis of polycyc...