Enantioselective and Regiodivergent Functionalization of N‐Allylcarbamates by Mechanistically Divergent Multicatalysis |
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Authors: | Dr Edward Richmond Ismat Ullah Khan Dr Joseph Moran |
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Institution: | 1. Institut de Science et d'Ingénierie Supramoleculaires (ISIS), Centre International de Recherche aux Frontières de la Chimie (icFRC), Université de Strasbourg, CNRS, Strasbourg, France;2. Department of Chemistry, Quaid i Azam University, Islamabad, Pakistan |
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Abstract: | A pair of mechanistically divergent multicatalytic reaction sequences has been developed consisting of nickel‐catalyzed isomerization of N‐allylcarbamates and subsequent phosphoric‐acid‐catalyzed enantioselective functionalization of the resulting intermediates. By appropriate selection of reaction partners, in situ generated imines and ene‐carbamates are mechanistically partitioned to yield opposing functionalized products. Formal α‐functionalization to give protected α‐arylamines is achieved upon enantioselective Friedel–Crafts reaction with arene nucleophiles, whereas formal β‐functionalization is achieved upon reaction with diarylimine electrophiles in an enantioselective Povarov‐4+2] cycloaddition. |
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Keywords: | Brø nsted acids carbamates imines isomerization multicatalysis nickel |
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