Three‐Component Reactions with (S)‐Methyl Pyroglutamate: An Efficient Way to Diversely Substituted Asymmetric Amidocyclohexenes |
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Authors: | Sandra Hübner Dirk Michalik Dr. Haijun Jiao Dr. Helfried Neumann Dr. Stefan Klaus Dirk Strübing Dr. Anke Spannenberg Dr. Matthias Beller Prof. Dr. |
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Affiliation: | Leibniz‐Institut für Katalyse e.V. an der Universit?t Rostock, Albert‐Einstein‐Str. 29a, 18059 Rostock, Germany, Fax: (+49)?381‐1281‐5000 |
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Abstract: | Chiral N‐dienyl lactams are crucial building blocks for the synthesis of complex organic compounds. However, their generation is rather challenging. This paper reports the novel one‐pot reaction of (S)‐methyl pyroglutamate as the a mide component with different a ldehydes and d ienophiles (AAD reaction) to give novel chiral 1‐amido‐2‐cyclohexenes. The corresponding N‐dienyl lactams generated in situ undergo subsequent Diels–Alder reactions in good yield and diastereoselectivity. The scope and limitations of the three‐component protocol were investigated. X‐ray and NMR spectroscopic analysis of the products as well as DFT calculations of the intermediates were also performed to explain the observed stereoselectivity and structural features. |
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Keywords: | chiral dienamides diastereoselectivity Diels– Alder reactions multicomponent reactions pyroglutamate |
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