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April 3, 2026Helvetica Chimica Acta0 citationsOpen Access

Memory of Chirality in Radical Addition–Translocation–Cyclization Cascades

CGChristian Simon GloorUniversity of Bern FDF. DénèsUniversity of Bern VSValentin SoulardUniversity of Bern

Key Points

Investigate the memory of chirality in radical addition-translocation-cyclization cascades using chiral nonracemic alkynes.
Utilized different hydrofunctionalization procedures.
Analyzed the effects of cyclization rate on chirality retention.
Assessed the impact of electrodeficient groups, particularly pentafluorobenzenesulfonyl.
Achieved high retention of configuration in chirality.
Enhanced cyclization rates were linked to favorable polar effects.
Demonstrated significant memory of chirality despite no conformational constraints.

Abstract

ABSTRACT The memory of chirality (MoC) in radical addition‐translocation‐cyclization (RATC) cascades involving chiral nonracemic alkynes has been examined using different hydrofunctionalization procedures. A high level of retention of configuration could be achieved when the rate of cyclization was enhanced due to favorable polar effects. The best system discovered so far was the use of the very electrodeficient pentafluorobenzenesulfonyl moiety. The MoC observed is remarkable if one considers that the system examined possesses no conformational constrain since only σ‐bonds are present in the backbone.

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