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DOI: 10.1055/s-0037-1611655
Organocatalytic Desymmetrisation of Fittig’s Lactones: Deuterium as a Reporter Tag for Hidden Racemisation
We are grateful for the financial support from NKFIH (K116150).Publikationsverlauf
Received: 12. Dezember 2018
Accepted: 17. Dezember 2018
Publikationsdatum:
24. Januar 2019 (online)
![](https://www.thieme-connect.de/media/synthesis/201905/lookinside/thumbnails/ss-2018-z0845-op_10-1055_s-0037-1611655-1.jpg)
Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue
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.
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