One-Pot, Tandem Reductive Amination/Alkylation-Cycloamidation for Lactam Synthesis from Keto or Amino Acids

P. Veeraraghavan Ramachandran*, Shivani Choudhary

*Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States, Email: chandranpurdue.edu

P. V. Ramachandran, S. Choudhary, J. Org. Chem., 2023, 88, 15956-15963.

DOI: 10.1021/acs.joc.3c01126

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Abstract

Monotrifluoroacetoxyborane-amines, prepared by treating borane-amines with trifluoroacetic acid, are efficient reagents for a one-pot, tandem reductive amination/alkylation-cycloamidation of keto or amino acids to provide 5-aryl or 5-methyl pyrrolidin-2-ones and 6-aryl or 6-methyl piperidin-2-ones.

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Key Words

γ-lactams, δ-lactams, TFAB-NEt₃

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ID: J42-Y2023