Title
A C=O⋅⋅⋅Isothiouronium Interaction Dictates Enantiodiscrimination in Acylative Kinetic Resolutions of Tertiary Heterocyclic Alcohols
Publication Date
2018
Journal Title
Angew Chem Int Ed Engl
Abstract
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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 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.
Volume Number
57
Issue Number
12
Pages
3200 - 3206
Document Type
Article
Status
Faculty
Facility
School of Medicine
Primary Department
Urology
PMID
DOI
10.1002/anie.201712456