De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy.

De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy. Research Abstract Details 

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De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy. Abstract Text:

Md Moinuddin Ahmed,Matthew S Mortensen,George A O'Doherty,

The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73-97% ee).

De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy. Publishing Authors By Initials

MM Ahmed,MS Mortensen,GA O'Doherty,

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De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy. Journal Published:

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

Journal: The Journal of organic chemistry

VOLUME: 71

Page Numbers: 7741-6

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ISSN: 0022-3263

DAY: 29

MONTH: Sep

YEAR: 2006

De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

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Grant and Affiliation Information for De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy.

AFFILIATION: Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.

Country: United States

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MEDLINETA: J Org Chem

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