Organocatalytic Desymmetrisation of Fittig's Lactones: Deuterium as a Reporter Tag for Hidden Racemisation

Péter Spránitz, Petra Soregi, Bence Béla Botlik, Máté Berta, Tibor Soós

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Abstract

Highly enantioselective desymmetrisation of Fittig's lactones with alcohols is promoted by bifunctional cinchona squaramides. The reactions were carried out with monodeuterated methanol to detect possible hidden racemisation of the stereogenic centre. Current evidence suggests that racemisation was not a relevant process for most substrates; partial erosion of enantioselectivity was only detected with ortho -substituted aryl derivates. The resultant glutaric acid derivatives possess a scaffold that is common in natural products and the compounds are also useful chiral building blocks for further synthetic endeavours.

Original languageEnglish
Pages (from-to)1263-1272
Number of pages10
JournalSynthesis (Germany)
Volume51
Issue number5
DOIs
Publication statusPublished - Jan 1 2019

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Keywords

  • Fittig's lactone
  • bifunctional organocatalysis
  • bislactone acylal
  • desymmetrization
  • racemization

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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