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Asymmetric hetero‐Diels‐Alder Reaction of trans ‐1‐Methoxy‐3‐trimethylsilyloxy‐buta‐1,3‐diene Catalyzed by Zinc Complexes
Author(s) -
Stefaniak Matylda,
Buda Szymon,
Mlynarski Jacek
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000822
Subject(s) - chemistry , diene , trifluoromethanesulfonate , trifluoroacetic acid , zinc , diels–alder reaction , catalysis , glyoxylate cycle , enantioselective synthesis , yield (engineering) , adduct , organic chemistry , stereochemistry , medicinal chemistry , natural rubber , materials science , metallurgy , enzyme
Asymmetric hetero‐Diels‐Alder reactions of Danishefsky's diene and glyoxylate/pyruvate esters catalyzed by readily available zinc triflate complex with BOX ligand afforded the corresponding adduct which upon treatment with trifluoroacetic acid furnished the hetero‐Diels‐Alder product in 91 % enantiomeric excess and 87 % isolated yield. This reaction was applied to the concise synthesis of six‐membered ulosonic acid C ‐glycoside.