Journal
TETRAHEDRON LETTERS
Volume 48, Issue 5, Pages 827-830Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2006.11.156
Keywords
Suzuki-Miyaura reaction; tosylate; 3-pyrrolin-2-one; pyrrol-2(5H)-one; pyrrolidin-2-one; tetramic acid
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A three step, convergent synthesis of 4-aryl-3-pyrrolin-2-ones from a tetramic acid has been developed. The key transformation utilized a Suzuki-Miyaura cross-coupling reaction between a 4-tosyloxy-3-pyrrolin-2-one and an arylboronic acid. This work also provides access to 4-arylpyrrolidin-2-ones, cyclic analogs of gamma-aminobutyric acid (GABA). Hydrogenation of 4-(4'-chloro-phenyl)-3-pyrrolin-2-one proceeded smoothly to give baclofen lactam. (c) 2006 Elsevier Ltd. All rights reserved.
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