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Synthesis of Acrylamides via the Doebner-Knoevenagel Condensation

Michael J. Zacuto*

*Drug Substance Development, Celgene Corporation, 556 Morris Avenue, Summit, New Jersey 07901, United States, Email:

M. J. Zacuto, J. Org. Chem., 2019, 84, 6465-6474.

DOI: 10.1021/acs.joc.9b00450

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The Doebner-Knoevenagel condensation enables a selective synthesis of acrylamides under mild conditions at ambient temperatures. The scalable reaction tolerates a wide range of functional groups, and affords the E-isomer with high selectivity. An organocatalytic mechanism has been proposed.

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proposed mechanism

Key Words

Doebner-Knoevenagel Condensation, Organocatalysis, α,β-Unsaturated Amides

ID: J42-Y2019