4.8 Article

Synthesis of aza-quaternary centers via Pictet-Spengler reactions of ketonitrones

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CHEMICAL SCIENCE
卷 12, 期 17, 页码 6181-6187

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc00882j

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  1. University of Chicago
  2. Jeff Metcalf Summer Internship Program

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This study presents a simple method for synthesizing a variety of products containing aza-quaternary centers by activating ketonitrones. The reaction process is mild, fast, and high-yielding, suitable for a diverse range of substrates, including those with electron-deficient substituents. Additionally, a catalytic asymmetric version has been developed, achieving good levels of enantioselectivity for several ketonitrones.
Despite the array of advances that have been made in Pictet-Spengler chemistry, particularly as it relates to the synthesis of beta-carboline derivatives of both natural and designed origin, the ability to use such reactions to generate aza-quaternary centers remains limited. Herein, we report a simple procedure that enables the synthesis of a variety of such products by harnessing the distinct reactivity profiles of ketonitrones as activated by commercially available acyl chlorides. Notably, the reaction process is mild, fast, and high-yielding (54-97%) for a diverse collection of substrates, including some typically challenging ones, such as indole cores with electron-deficient substituents. In addition, by deploying an acyl bromide in combination with a thiourea promoter, a catalytic, asymmetric version has been established, leading to good levels of enantioselectivity (up to 83% ee) for several ketonitrones. Finally, the resultant N-O bonds within the products can also be functionalized in several unique ways, affording valuable complementarity to existing Pictet-Spengler variants based on the use of imines.

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