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

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 racemisa...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 51; no. 5; pp. 1263 - 1272
Main Authors Spránitz, Péter, Sőregi, Petra, Botlik, Bence Béla, Berta, Máté, Soós, Tibor
Format Journal Article
LanguageEnglish
Published Stuttgart · New York Georg Thieme Verlag 01.03.2019
Thieme Medical Publishers
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
bislactone acylal
bifunctional organocatalysis
desymmetrization
racemization
Fittig’s lactone
BISLACTONES
MECHANISM
MALONATE
BILOBALIDE
Fittig's lactone
MICHAEL ADDITION
ACID CATALYZED DESYMMETRIZATION
DERIVATIVES
ANHYDRIDE
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1611655