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

29329500

DOI

10.1002/anie.201712456

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