A Lewis Acid−Lewis Base Bifunctional Catalyst from a New Mixed Ligand

Covalent attachment of quinine to a salen framework through a racemic linker gave a new mixed ligand in a 1:1 diastereomeric mixture, from which an active Lewis acid−Lewis base (LA*−LB*) bifunctional catalyst derived from Co(II) was discovered by the screening of metal complexes. The remarkable intr...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 4; pp. 567 - 570
Main Authors Lin, Yun-Ming, Boucau, Julie, Li, Zhongtao, Casarotto, Virginie, Lin, Jinzhen, Nguyen, Annie N, Ehrmantraut, Jessica
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.02.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
ASYMMETRIC-SYNTHESIS
BETA-LACTONES
SCHIFF-BASE
NUCLEOPHILE
ALDEHYDES
ENANTIOSELECTIVE ADDITION
KETENE
STRECKER REACTION
METAL-COMPLEXES
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Summary:Covalent attachment of quinine to a salen framework through a racemic linker gave a new mixed ligand in a 1:1 diastereomeric mixture, from which an active Lewis acid−Lewis base (LA*−LB*) bifunctional catalyst derived from Co(II) was discovered by the screening of metal complexes. The remarkable intramolecular bifunctional catalytic activity (1 mol % catalyst loading) of the new catalyst was demonstrated using a proof-of-principle reaction.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0626903