A convenient, facile, and one-pot methodology for the synthesis of α-carbolines from Baylis-Hillman (BH) acetates, involving three steps (reactions), (1) mono alkylation of 2-nitroarylacetonitriles with BH-acetates, (2) reduction of nitro group into amino group using Fe/AcOH and (3) formation of two (five and six membered) rings, is presented. This methodology is successfully applied to the synthesis of bioactive alkaloid neocryptolepine.
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Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita-Baylis-Hillman Acetates.
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College of Advanced Interdisciplinary Science and Technology (CAIST), Henan University of Technology, Zhengzhou 450001, Henan, P. R. China.
We present an iron-photocatalyzed decarboxylative alkylation strategy involving carboxylic acids and Morita-Baylis-Hillman (MBH) acetates to synthesize -type tri- and tetrasubstituted alkenes with moderate to excellent stereoselectivity (/ ratio up to >19:1). This method is applicable to a broad range of structurally diverse primary, secondary, and tertiary alkyl carboxylic acids, as well as complex pharmaceutical and natural carboxylic acids, achieving efficient alkylation of various MBH acetates under mild conditions (>60 examples, with yields up to 96%). This approach offers a powerful strategy for streamlined alkylation.
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