Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst.

Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst. Research Abstract Details 

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Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst. Abstract Text:

Barry M Trost,Takashi Mino,

A dinuclear asymmetric zinc catalyst generated by mixing a 2:1 ratio of diethylzinc and 2,6-bis[5-2-diarylhydroxy methyl-1-pyrrolidinyl]-4-methylphenol has been contrasted with enzymes for the desymmetrization of some meso diols. The best ligand has a p-biphenylyl group as the aromatic substituent defining the chiral space. A series of 2-substituted propanediols were examined. The best acyl transfer agent proved to be vinyl benzoate. Diacylation normally did not occur. The phenyl substituted substrate gave 91-95% ee which compares favorably with the best ee of 92% reported for an enzymatic desymmetrization. The methyl substituted substrate gave significantly better results with the dinuclear zinc catalyst (89% yield, 82% ee) as compared to the best enzymatic esterification (70% yield, 60% ee). One case of a 1,4-diol, cis-1,2-bis(hydroxymethyl) cyclohexane, also gave much better results with the dinuclear zinc catalysts (93% yield, 91% ee) as compared to the reported enzymatic process (44% yield, 7% ee). A model to rationalize the results is presented.

Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst. Publishing Authors By Initials

BM Trost,T Mino,

For similar natural sciences: chemistry: chemistry, organic: isomerism: stereoisomerism research abstracts see: natural sciences: chemistry: chemistry, organic: isomerism: stereoisomerism research

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Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 125

Page Numbers: 2410-1

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 5

MONTH: Mar

YEAR: 2003

Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 7503056

Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst. Keywords Mesh Terms:

KEYWORDS: Stereoisomerism

MESH TERMS: chemistry

Chemical & Substance for Abstract: Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst. Information

Substance Name: diethylzinc

Registry Number: 557-20-0

Grant and Affiliation Information for Desymmetrization of meso 1,3- and 1,4-diols with a dinuclear zinc asymmetric catalyst.

AFFILIATION: Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu

Country: United States

AGENCY: United States NIGMS

GRANT: GM 33049

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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