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Determination of the Absolute Configuration of ?-Chiral Primary Alcohols Using the Competing Enantioselective Conversion Method.

ABSTRACT: A method for determining the absolute configuration of ?-chiral primary alcohols has been developed. Enantioenriched alcohols were acylated in the presence of either enantiomer of the enantioselective acylation catalyst HBTM, and the faster reaction was determined by measuring product conversion using 1H NMR spectroscopic analysis. An empirical mnemonic was developed that correlates the absolute configuration of the alcohol to the faster reacting catalyst. Successful substrates for this method include primary alcohols that bear a "directing group" on the stereogenic center; directing groups include arenes, heteroarenes, enones, and halides.

SUBMITTER: Burns AS

PROVIDER: S-EPMC6364845 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Determination of the Absolute Configuration of β-Chiral Primary Alcohols Using the Competing Enantioselective Conversion Method.

Burns Alexander S AS Wagner Alexander J AJ Fulton Jennifer L JL Young Kyle K Zakarian Armen A Rychnovsky Scott D SD

Organic letters 20170516 11

A method for determining the absolute configuration of β-chiral primary alcohols has been developed. Enantioenriched alcohols were acylated in the presence of either enantiomer of the enantioselective acylation catalyst HBTM, and the faster reaction was determined by measuring product conversion using <sup>1</sup>H NMR spectroscopic analysis. An empirical mnemonic was developed that correlates the absolute configuration of the alcohol to the faster reacting catalyst. Successful substrates for th ...[more]

PMID: 28508638

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