Catalyst-Controlled, Site-Selective Functionalization of Levoglucosan Analogues Mediated by Chiral Zinc Diamine Complexes

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

In this work, we developed a site-selective functionalization of levoglucosan analogues. This strategy used simple zinc diamine complexes for regioselective at O2 or O4. Successful transformations monotosyl analogues allowed the preparation useful intermediates in carbohydrate chemistry, such as four protected Černý epoxides and three amino sugars. unique method represents rare use desymmetrization 1,3-diols.

Язык: Английский

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Site-Switchable Alkylation of Carbohydrates Controlled by Inexpensive Metal Ion Catalysts

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 7414 - 7428

Опубликована: Апрель 20, 2025

Язык: Английский

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Unified Strategy for the Concise Total Syntheses of All Six 3″-O-Acyl Quercitrins Based on Regioselective Acylation Catalyzed by Boronic Acid

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 3, 2025

The naturally occurring 3″-O-acylquercitrin family exhibits a range of biological activities with significant potential health and medical benefits. Herein, we present unified strategy for concise total syntheses all six known natural products─namely, 3″-O-galloylquercitrin, 3″-O-(E)-cinnamoylquercitrin, 3″-O-(E)-coumaroylquercitrin, 3″-O-(E)-feruloylquercitrin, 3″-O-acetylquercitrin, 3″-O-tigloylquercitrin─based on regioselective acylation carbohydrates catalyzed by N-methylimidazole-containing boronic acid. core advancement in this approach is late-stage catalytic functionalization common synthetic intermediate, enabling efficient access to the products.

Язык: Английский

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Cooperative Diarylborinic Acid/Chloride-Catalyzed Formal S_Ni Reaction of cis-4-Hydroxymethyl-1,2-Cyclopentene Oxides

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Сен. 26, 2024

A catalytic formal S

Язык: Английский

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