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Updated: May 30, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Catalyst-Controlled, Site-Selective Functionalization of Levoglucosan Analogues Mediated by Chiral Zinc Diamine
Sam Bahadori1, Christina Leclerc1, Jacob St-Gelais1
1Département de Chimie, 1045 av. De la Médecine, Université Laval, Québec City, Quebec G1 V 0A6, Canada.
Abstract:
In this work, we developed a site-selective functionalization of levoglucosan analogues. This strategy used simple zinc diamine complexes for regioselective functionalization at O2 or O4. Successful transformations of monotosyl analogues allowed the preparation of useful intermediates in carbohydrate chemistry, such as four protected Černý epoxides and three protected amino sugars. This unique method represents a rare use of zinc for the desymmetrization of 1,3-diols.
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