Tandem Gold Self‐Relay Catalysis for the Synthesis of 2,3‐Dihydropyridin‐4(1 H)‐ones: Combination of σ and π Lewis Acid Properties of Gold Salts |
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| Authors: | Prof Santos Fustero Javier Miró Dr María Sánchez‐Roselló Dr Carlos del Pozo |
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| Affiliation: | 1. Departamento de Química Orgánica, Universidad de Valencia, 46100‐Burjassot (Spain);2. Laboratorio de Moléculas Orgánicas, Centro de Investigación Principe Felipe, 46012‐Valencia (Spain) |
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| Abstract: | The dual ability of gold salts to act as π‐ and σ Lewis acids has been exploited in a tandem self‐relay catalysis. Thus, triphenylphosphanegold(I) triflate mediated the intramolecular carbonyl addition of the amide functionality of homoprogargyl amides to a triple bond. The formation of a σ complex of the gold salt with the intermediate oxazine promoted a nucleophilic addition followed by a Petasis–Ferrier rearrangement. This tandem protocol, catalyzed by the same gold salt under the same reaction conditions, gave rise to the efficient synthesis of 2,3‐dihydropyridin‐4‐(1 H)‐ones, which contain a cyclic quaternary α‐amino acid unit. The asymmetric version was performed by generating the starting materials from the corresponding sulfinylimines. |
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| Keywords: | alkaloids autocatalysis gold Lewis acids transition‐metal catalysis |
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