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Determination of absolute configuration using kinetic resolution catalysts.

ABSTRACT: A new method was developed to assign the absolute configuration of molecules using kinetic resolution catalysts. Secondary alcohols were acylated in the presence of Birman's S-HBTM and R-HBTM catalysts, and the fast-reacting catalyst was identified by NMR analysis of the reaction mixture. A mnemonic was developed to assign configuration based on the identity of the fast-reacting catalyst. The method uses only 1-3 mg of alcohol, and it is more convenient than the Mosher method. The kinetic resolution strategy may be extended to other classes of molecules.

SUBMITTER: Wagner AJ

PROVIDER: S-EPMC3179685 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Determination of absolute configuration using kinetic resolution catalysts.

Wagner Alexander J AJ David Jonathan G JG Rychnovsky Scott D SD

Organic letters 20110721 16

A new method was developed to assign the absolute configuration of molecules using kinetic resolution catalysts. Secondary alcohols were acylated in the presence of Birman's S-HBTM and R-HBTM catalysts, and the fast-reacting catalyst was identified by NMR analysis of the reaction mixture. A mnemonic was developed to assign configuration based on the identity of the fast-reacting catalyst. The method uses only 1-3 mg of alcohol, and it is more convenient than the Mosher method. The kinetic resolu ...[more]

PMID: 21776975

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