Palladium-catalyzed arylation of alpha-methylene-gamma-butyrolactone: 3-benzylfuran-2(5H)-ones vs (Z)-benzylidene-gamma-butyrolactones and their reduction to 3-benzyl-gamma-butyrolactones

Org Lett. 2000 Jan;2(1):69-72. doi: 10.1021/ol9912130.

Abstract

[reaction: see text] The palladium-catalyzed arylation of the alpha-methylene-gamma-butyrolactone proceeds in good yields and may be directed toward the synthesis of 3-benzylfuran-2(5H)-ones when the starting aryl iodides contain strongly electron-withdrawing groups. The combined palladium-catalyzed arylation/hydrogenation of the alpha-methylene-gamma-butyrolactone represents a new simple entry into functionalized alpha-benzyl-gamma-butyrolactones.