Trans-Stereoselectivity in the Reaction between Homophthalic Anhydride and Imines

The reaction between homophthalic anhydride and imines in the presence of TiCl4 and diisopropyl ethyl amine is trans-selective. Under these conditions, the reaction using homochiral imines can be highly diastereoselective, thus allowing the synthesis of enantiopure 1,2,3,4-tetrahydro-1-oxoquinoline-...

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Published inOrganic letters Vol. 10; no. 21; pp. 4759 - 4762
Main Authors Vara, Yosu, Bello, Tamara, Aldaba, Eneko, Arrieta, Ana, Pizarro, José L, Arriortua, María I, Lopez, Xabier, Cossío, Fernando P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.11.2008
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Imines - chemistry
Models, Molecular
Molecular Structure
Phthalic Anhydrides - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
DENSITY
REAGENT
BETA-AMINO ESTERS
ALDIMINES
TITANIUM ENOLATE
ALDOL REACTIONS
INDENOISOQUINOLINE
TOPOISOMERASE-I INHIBITORS
EFFICIENT
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Summary:The reaction between homophthalic anhydride and imines in the presence of TiCl4 and diisopropyl ethyl amine is trans-selective. Under these conditions, the reaction using homochiral imines can be highly diastereoselective, thus allowing the synthesis of enantiopure 1,2,3,4-tetrahydro-1-oxoquinoline-4-carboxylic acids.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol801757r