Rhodium-catalyzed 1,4-addition of arylboronic acids to 3-benzylidene-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives

J Org Chem. 2015 Mar 20;80(6):3264-9. doi: 10.1021/jo502784h. Epub 2015 Mar 2.

Abstract

7-Azaindoles are versatile building blocks, especially in medicinal chemistry, where they serve as bioisosteres of indoles or purines. Herein, we present a novel rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to 3-benzylidene-1H-pyrrolo[2,3-b]pyridin-2(3H)-ones, as these substrates are exocyclic methylene lactamyl Michael acceptors. Ten new original derivatives of 1H-pyrrolo[2,3-b]pyridin-2(3H)-one have been obtained.