Journal
ORGANIC LETTERS
Volume 23, Issue 3, Pages 1118-1122Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00067
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Funding
- National Natural Science Foundation of China [21702080]
- Natural Science Foundation of Jiangxi Province of China [20181BAB213003]
- Open Project Program of Key Laboratory of Functional Small Organic Molecule, Ministry of Education, Jiangxi Normal University [KLFS-KF-201603]
- foundation of Jiangxi Educational Committee [170223]
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The chiral phosphoric acid-catalyzed enantioselective condensation of 2,2-disubstituted cyclobutane-1,3-diones with a primary amine provides a mild and efficient method for constructing quaternary carbon-containing cyclobutanes with good to high yields and enantioselectivities. This reaction is the first of its kind, representing a catalytic desymmetrizing carbonyl-amine condensation reaction as well as a catalytic desymmetrizing reaction of prochiral cyclobutane-1,3-dione.
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.
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