Palladium-Catalyzed Enantioselective Stereodivergent Desymmetrization of Cyclic 1,4-Allyldiboronates

In the presence of a chiral palladium-based catalyst, 1,4-diboryl-2-alkenes undergo enantioselective cross-coupling that results in desymmetrization of the substrate structure. Depending on the reaction conditions and the choice of ligand, the reaction can occur with <i>cis</i> or <i>trans</i> selectivity, allowing the construction of an array of different substituted chiral carbocycles in an enantiomerically enriched fashion.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-02-04
DOI
https://doi.org/10.1021/jacs.4c16020
Citations
7
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
6.55

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article

Palladium-Catalyzed Enantioselective Stereodivergent Desymmetrization of Cyclic 1,4-Allyldiboronates

Robert A. Singer, Lorenzo D. Battistoni, Christophe Allais, James P. Morken et al.
7 citations
Journal of the American Chemical Society
Organoboron and organosilicon chemistry
6.55
article

Palladium-Catalyzed Enantioselective Stereodivergent Desymmetrization of Cyclic 1,4-Allyldiboronates

Robert A. Singer, Lorenzo D. Battistoni, Christophe Allais, James P. Morken, Hao Liang, Sergei Tcyrulnikov
article en
7 citations

Abstract

In the presence of a chiral palladium-based catalyst, 1,4-diboryl-2-alkenes undergo enantioselective cross-coupling that results in desymmetrization of the substrate structure. Depending on the reaction conditions and the choice of ligand, the reaction can occur with <i>cis</i> or <i>trans</i> selectivity, allowing the construction of an array of different substituted chiral carbocycles in an enantiomerically enriched fashion.

Journal of the American Chemical SocietyVol. 147(7)
Boston College (US), Pfizer (United States) (US)
Division of Chemistry
Openalex Percentile: Top 4%
Organoboron and organosilicon chemistry
6.55
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