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      General Synthesis of 3‐Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Isosteres**

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          Abstract

          A general approach to 3‐azabicyclo[3.1.1]heptanes by reduction of spirocyclic oxetanyl nitriles was developed. The mechanism, scope, and scalability of this transformation were studied. The core was incorporated into the structure of the antihistamine drug Rupatidine instead of the pyridine ring, which led to a dramatic improvement in physicochemical properties.

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          Photoinduced decarboxylative borylation of carboxylic acids

          Varinder K Aggarwal, Tatsuya Mutsuga, Eddie Myers … (2017)
          The conversion of widely available carboxylic acids into versatile boronic esters would be highly enabling for synthesis. We found that this transformation can be effected by illuminating the N-hydroxyphthalimide ester derivative of the carboxylic acid under visible light at room temperature in the presence of the diboron reagent bis(catecholato)diboron. A simple workup allows isolation of the pinacol boronic ester. Experimental evidence suggests that boryl radical intermediates are involved in the process. The methodology is illustrated by the transformation of primary, secondary, and tertiary alkyl carboxylic acids as well as a diverse range of natural-product carboxylic acids, thereby demonstrating its broad utility and functional group tolerance.
          Article 0 comments Cited 136 times – based on 0 reviews     Review now
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            The use of spirocyclic scaffolds in drug discovery.

            Yajun Zheng, Colin Tice, Suresh Singh (2014)
            Owing to their inherent three-dimensionality and structural novelty, spiro scaffolds have been increasingly utilized in drug discovery. In this brief review, we highlight selected examples from the primary medicinal chemistry literature during the last three years to demonstrate the versatility of spiro scaffolds. With recent progress in synthetic methods providing access to spiro building blocks, spiro scaffolds are likely to be used more frequently in drug discovery.
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              Organic chemistry. Strain-release amination.

              Ryan Gianatassio, Justin Lopchuk, Jie Wang … (2016)
              To optimize drug candidates, modern medicinal chemists are increasingly turning to an unconventional structural motif: small, strained ring systems. However, the difficulty of introducing substituents such as bicyclo[1.1.1]pentanes, azetidines, or cyclobutanes often outweighs the challenge of synthesizing the parent scaffold itself. Thus, there is an urgent need for general methods to rapidly and directly append such groups onto core scaffolds. Here we report a general strategy to harness the embedded potential energy of effectively spring-loaded C-C and C-N bonds with the most oft-encountered nucleophiles in pharmaceutical chemistry, amines. Strain-release amination can diversify a range of substrates with a multitude of desirable bioisosteres at both the early and late stages of a synthesis. The technique has also been applied to peptide labeling and bioconjugation.
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                Author and article information

                Contributors
                Pavel K. Mykhailiuk: (View ORCID Profile)
                Journal
                Title: Angewandte Chemie International Edition
                Abbreviated Title: Angew Chem Int Ed
                Publisher: Wiley
                ISSN (Print): 1433-7851
                ISSN (Electronic): 1521-3773
                Publication date Created: September 25 2023
                Publication date (Electronic): June 15 2023
                Publication date (Print): September 25 2023
                Volume: 62
                Issue: 39
                Affiliations
                [1 ] Enamine Ltd. Chervonotkatska 60 02094 Kyiv Ukraine
                [2 ] Institute of Bioorganic Chemistry and Petrochemistry National Academy of Sciences of Ukraine Akademika Kukharya, 1 02094 Kyiv Ukraine
                [3 ] Bienta Chervonotkatska 78 02094 Kyiv Ukraine
                [4 ] Department of Chemistry Molecular Sciences Research Hub White City Campus Imperial College London 82 Wood Lane London W12 0BZ UK
                Article
                DOI: 10.1002/anie.202304246
                SO-VID: 3b89032b-609b-4cb7-80df-5c23969ce0da
                Copyright © © 2023
                License:

                http://creativecommons.org/licenses/by/4.0/

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