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A C=O•••isothiouronium interaction dictates enantiodiscrimination in acylative kinetic resolution of tertiary heterocyclic alcohols

Research output: Contribution to journalArticle

Author(s)

Mark D. Greenhalgh, Samuel M. Smith, Daniel M. Walden, James E. Taylor, Zamira Brice, Emily R. T. Robinson, Charlene Fallan, David B. Cordes, Alexandra M. Z. Slawin, H. Camille Richardson, Markas A. Grove, Paul Ha-Yeon Cheong, Andrew D. Smith

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Abstract

A combination of experimental and computational studies have identified a C=O•••isothiouronium interaction as key to efficient enantiodiscrimination in the kinetic resolution of tertiary heterocyclic alcohols bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. This discrimination was exploited in the isothiourea-catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols (38 examples, s up to > 200). The reaction proceeds at low catalyst loadings (generally 1 mol%) using either isobutyric or acetic anhydride as the acylating agent under mild conditions
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Original languageEnglish
Pages (from-to)3200-3206
JournalAngewandte Chemie International Edition
Volume57
Issue number12
Early online date19 Feb 2018
DOIs
Publication statusPublished - 12 Mar 2018

    Research areas

  • Kinetic resolution, Lewis bases, Organocatalysis, Tertiary alcohols, Acylation

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