Short synthesis of 4-aryl-3-pyrrolin-2-ones

SJP Yoon-Miller, SM Opalka, ET Pelkey

Index: Yoon-Miller, Sarah J.P.; Opalka, Suzanne M.; Pelkey, Erin T. Tetrahedron Letters, 2007 , vol. 48, # 5 p. 827 - 830

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Citation Number: 19

Abstract

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 γ-aminobutyric acid (GABA). Hydrogenation of 4-(4′-chlorophenyl)-3-pyrrolin-2-one proceeded smoothly to give ...