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

The enantioselective preparation of a range of perfluoroalkyl-substituted β-lactones through an isothiourea (HyperBTM) catalysed reaction using symmetric anhydrides as ammonium enolate precursors and perfluoroalkylketones (R F = CF 3 , C 2 F 5 , C 4 F 9 ) is reported. Following optimisation, high diastereo- and enantioselectivity was observed for β-lactone formation using C 2 F 5 - and C 4 F 9 -substituted ketones at room temperature (26 examples, up to &gt;95 : 5 dr and &gt;99 : 1 er), whilst -78 °C was necessary for optimal dr and er with CF 3 -substituted ketones (11 examples, up to &gt;95 : 5 dr and &gt;99 : 1 er). Derivatisation of the β-lactones through ring-opening, as well as a two-step conversion to give perfluoroalkyl-substituted oxetanes, is demonstrated without loss of stereochemical integrity. Density functional theory computations, alongside 13 C natural abundance KIE studies, have been used to probe the reaction mechanism with a concerted asynchronous [2 + 2]-cycloaddition pathway favoured over a stepwise aldol-lactonisation process.

chemical science

Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones <i>via</i> a concerted asynchronous [2 + 2] cycloaddition: a synthetic and computational study

Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones via a concerted asynchronous [2 + 2] cycloaddition: a synthetic and computational study