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- Title
A C=O⋅⋅⋅Isothiouronium Interaction Dictates Enantiodiscrimination in Acylative Kinetic Resolutions of Tertiary Heterocyclic Alcohols.
- Authors
Greenhalgh, Mark D.; Smith, Samuel M.; Walden, Daniel M.; Taylor, James E.; Brice, Zamira; Robinson, Emily R. T.; Fallan, Charlene; Cordes, David B.; Slawin, Alexandra M. Z.; Richardson, H. Camille; Grove, Markas A.; Cheong, Paul Ha‐Yeon; Smith, Andrew D.
- Abstract
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, <italic>s</italic> factors up to >200). The reaction proceeds at low catalyst loadings (generally 1 mol %) with either isobutyric or acetic anhydride as the acylating agent under mild conditions.
- Subjects
KINETIC resolution; ALCOHOL; ACETIC anhydride
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 12, p3254
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201712456