English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Plus annual

Presents the access of premium content as premium feature

Premium Content

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools annual

Global: Zendy Free Plan

Global: Zendy Tools monthly

Global: Zendy Plus monthly

A regioselective epoxy alcohol cyclization promoted by the combination of neutral water and a tetrahydropyran template was investigated through a series of mechanistic experiments carried out on an epoxy alcohol containing a tetrahydropyran ring (1a) and its carbocyclic congener (1b). In contrast to 1a, cyclizations of 1b were unselective and displayed significantly faster reaction rates suggesting that the tetrahydropyran oxygen in 1a is requisite for regioselective cyclization. Reactions for both substrates were shown to occur in solution and under kinetic control without significant influence from hydrophobic effects. Kinetic measurements carried out in water/dimethyl sulfoxide mixtures suggest that 1b reacts exclusively through an unselective pathway requiring one water molecule more than what is required to solvate the epoxy alcohol. Similar experiments for 1a suggest a competition between an unselective and a selective pathway requiring one and two water molecules in excess of those required to solvate 1a, respectively. The selective pathway observed for 1a but not in 1b is rationalized by electronic and conformational differences between the two compounds.

On the Synergism Between H2O and a Tetrahydropyran Template in the Regioselective Cyclization of an Epoxy Alcohol

On the Synergism Between H₂O and a Tetrahydropyran Template in the Regioselective Cyclization of an Epoxy Alcohol