Catalytic Enantioselective Desymmetrization of Cyclobutane-1,3-diones by Carbonyl-Amine Condensation

A chiral phosphoric acid-catalyzed enantioselective condensation of 2,2-disubstituted cyclobutane-1,3-diones with a primary amine is described. This reaction offered a mild and efficient protocol for constructing quaternary carbon-containing cyclobutanes in good to high yields and enantioselectiviti...

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Published inOrganic letters Vol. 23; no. 3; pp. 1118 - 1122
Main Authors Wen, Kai-Ge, Liu, Chao, Wei, Dong-Hui, Niu, Yan-Fei, Peng, Yi-Yuan, Zeng, Xing-Ping
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A chiral phosphoric acid-catalyzed enantioselective condensation of 2,2-disubstituted cyclobutane-1,3-diones with a primary amine is described. This reaction offered a mild and efficient protocol for constructing quaternary carbon-containing cyclobutanes in good to high yields and enantioselectivities. This reaction is the first catalytic desymmetrizing carbonyl-amine condensation reaction and also represents the first catalytic desymmetrizing reaction of prochiral cyclobutane-1,3-dione.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00067