NHC-Catalyzed/Titanium(IV)−Mediated Highly Diastereo- and Enantioselective Dimerization of Enals

An NHC-catalyzed, diastereo- and enantioselective dimerization of enals has been developed. The use of Ti(Oi-Pr)4 is a key element for the reactivity and selectivity of this process. The cyclopentenes are obtained with high levels of diastereo- and enantioselectivity and their synthetic utility is d...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 5; pp. 1068 - 1071
Main Authors Cohen, Daniel T, Cardinal-David, Benoit, Roberts, John M, Sarjeant, Amy A, Scheidt, Karl A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.03.2011
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Dimerization
Lewis Acids - chemistry
Methane - analogs & derivatives
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Titanium - chemistry
SALT
CATALYSIS
CARBENES
ALPHA,BETA-UNSATURATED ALDEHYDES
SECONDARY STRUCTURES
THIAMIN DIPHOSPHATE
EFFICIENT SYNTHESIS
BETA-PEPTIDE
STEREOSELECTIVE-SYNTHESIS
BENZOIN
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Summary:An NHC-catalyzed, diastereo- and enantioselective dimerization of enals has been developed. The use of Ti(Oi-Pr)4 is a key element for the reactivity and selectivity of this process. The cyclopentenes are obtained with high levels of diastereo- and enantioselectivity and their synthetic utility is demonstrated by functionalization of the product alkene.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol103112v