A Mild and Selective Method for the Hydrolysis of Esters with Trimethyltin Hydroxide

Mild, selective, and efficient: A new method that involves the use of trimethyltin hydroxide for the hydrolysis of specific ester groups allows chemists to steer clear of unwanted elimination reactions and epimerizations. For example, the conversion of ester 1 into carboxylic acid 2 takes place unde...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-02, Vol.44 (9), p.1378-1382
Main Authors: Nicolaou, K. C., Estrada, Anthony A., Zak, Mark, Lee, Sang Hyup, Safina, Brian S.
Format: Article
Language:English
Subjects:
Chemistry, Organic - methods
epimerization
Esters - chemistry
Hydrolysis
Molecular Structure
synthetic methods
tin
Trimethyltin Compounds - chemistry
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Summary:Mild, selective, and efficient: A new method that involves the use of trimethyltin hydroxide for the hydrolysis of specific ester groups allows chemists to steer clear of unwanted elimination reactions and epimerizations. For example, the conversion of ester 1 into carboxylic acid 2 takes place under mild conditions, with nearly complete retention of stereochemical integrity. 1,2‐DCE=1,2‐dichloroethane.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200462207