Unified Approach to Diverse Fused Fragments via Catalytic Dehydrative Cyclization

Abstract

A range of highly functionalized polycyclic fragments have been synthesized, employing a catalytic dehydrative cyclization. A range of nucleophiles are shown to be successful, with the reaction producing numerous high value motifs.

A robust heterogeneous chiral phosphoric acid enables multi decagram scale production of optically active N,S-ketals

“… 15 This reaction is particularly interesting for our purpose since full conversion to the racemate was reported after just a few minutes of reaction even in the absence of any catalyst. Additionally, similar processes have been used to synthesize active pharmaceutical ingredients ( Scheme 1C ), 16 increasing the interest in merging this asymmetric methodology with continuous flow processing.…”

A Robust Heterogeneous Chiral Phosphoric Acid Enables Multi Decagram Scale Production Of Optically Active N, S-Ketals

“…50 This reaction is particularly interesting for our purpose since full conversion to the racemate was reported after just a few minutes of reaction even in the absence of any catalyst. Additionally, similar processes have been used to synthesize active pharmaceutical ingredients (Scheme 1, C), [51][52][53][54] increasing the interest in merging this asymmetric methodology with continuous flow processing.…”

Aza-[4 + 2] cycloadditions employing catalytically derivedN-acyliminium ions

“…Our work began by taking advantage of our previously reported methodology to access N-acyliminium ions via catalytic dehydration. [11][12][13][14] We therefore began our investigation using these conditions, employing hydroxyisoindolinone 1 and dimethylbutadiene (2a) as model substrates (Table 1). As shown, optimisation of temperature, solvent, and catalyst loading led to conditions that afforded the [4 + 2] product in high isolated yield.…”