Synthesis of a Fluorous Ligand and Its Application for Asymmetric Addition of Dimethylzinc to Aldehydes

A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on the addition of dimethylzinc to aldehydes. This ligand will be useful for synthesis of bioactive compounds with a methyl carbinol moiety. It could be recycled without using...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 10; pp. 1927 - 1929
Main Authors Sokeirik, Yasser S, Mori, Hiroyuki, Omote, Masaaki, Sato, Kazuyuki, Tarui, Atsushi, Kumadaki, Itsumaro, Ando, Akira
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.05.2007
Amer Chemical Soc
Subjects
Aldehydes - chemical synthesis
Aldehydes - chemistry
Chemistry
Chemistry, Organic
Chromatography, High Pressure Liquid
Dioxolanes - chemistry
Fluorine Compounds - chemical synthesis
Fluorine Compounds - chemistry
Ligands
Methanol - analogs & derivatives
Methanol - chemistry
Methylation
Molecular Structure
Organometallic Compounds - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
KETONES
AXIALLY DISSYMMETRIC LIGAND
REAGENTS
ME2ZN
HIGHLY ENANTIOSELECTIVE ADDITION
DIALKYLZINCS
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Summary:A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on the addition of dimethylzinc to aldehydes. This ligand will be useful for synthesis of bioactive compounds with a methyl carbinol moiety. It could be recycled without using a fluorous solvent or a fluorous column.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070466n