Desymmetrization of aziridine with malononitrile using cinchona alkaloid amide/zinc(II) catalysts

The catalytic enantioselective desymmetrization of aziridines with malononitrile has been developed. Good yield and enantioselectivity were obtained by using cinchona alkaloid amide/Zn(II) catalysts. The obtained product can be converted to beta-aminoester, beta-aminoamide and triamide compounds.

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 53; no. 11; pp. 1817 - 1820
Main Authors Shiomi, Noriyuki, Kuroda, Mami, Nakamura, Shuichi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 02.02.2017
Subjects
Alkaloids
Amides
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Malononitrile
Physical Sciences
Science & Technology
VINYLOGOUS MANNICH REACTION
SCHIFF-BASE CATALYSIS
N-ACYLAZIRIDINES
RING-OPENING REACTIONS
PALLADIUM PINCER COMPLEXES
MESO-AZIRIDINES
ENANTIOSELECTIVE MICHAEL ADDITION
ACID HALF THIOESTERS
GENERATED MAGNESIUM CATALYST
CONJUGATE ADDITION
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Summary:The catalytic enantioselective desymmetrization of aziridines with malononitrile has been developed. Good yield and enantioselectivity were obtained by using cinchona alkaloid amide/Zn(II) catalysts. The obtained product can be converted to beta-aminoester, beta-aminoamide and triamide compounds.
Bibliography:KAKEN
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ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc09457k